Oct. 2016, 平成27年度「日本化学会北海道支部奨励賞」　　　　　　　　　　　　　　　

Development and Mechanistic Insights into Nef Reaction for Preparation of Aldehydes Using Singlet Oxygen
Ira Novita Sari, Bobo Yan, Tatsuya Morozumi, Yuichi Kamiya, Taiki Umezawa
Organic Letters, American Chemical Society (ACS), 17 Apr. 2025
Scientific journal

Synthetic Study on Mytilipin C and Development of New Synthetic Methodology toward Total Synthesis
Taiki Umezawa
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2025
Scientific journal

Chemoselective Preparation of Alkynes from Vicinal and Geminal Dibromoalkenes.
Hyuga Okumura, Nurcahyo Iman Prakoso, Tatsuya Morozumi, Taiki Umezawa
Organic letters, 26, 46, 9817, 9821, 22 Nov. 2024, [International Magazine]
English, Scientific journal, The reductive conversion of vicinal and geminal dibromoalkenes into the corresponding alkynes with iPrMgCl-LiCl (Turbo Grignard reagent) is described. This reaction proceeded in the presence of various functional groups such as ethers, esters, or carbamates under mild conditions in high yields. Due to the selective reactivity, the easily prepared vic-dibromoalkene is considered to be a protecting group of alkyne toward an electrophile. Although butyl lithium has been widely used for the conversion of gem-dibromoalkenes into alkynes in the Corey-Fuchs alkyne synthesis, we report here alternative mild and chemoselective reaction conditions for alkyne synthesis.

Doubly Homologated Tyrosine-Containing Peptides from the Cyanobacterium Microcystis aeruginosa NIES-4285 and Their Biosynthesis
Chin-Soon Phan, Zhengyi Ling, Jakia Jerin Mehjabin, Kenichi Matsuda, Nurcahyo Iman Prakoso, Taiki Umezawa, Toshiyuki Wakimoto, Tatsufumi Okino
Journal of Natural Products, American Chemical Society (ACS), 30 Oct. 2024
Scientific journal

Synthesis and Conformational Analysis of α,β-Dichlorocarbonyl Compounds
Shunta Kobayashi, Nurcahyo Iman Prakoso, Xin Zheng, Shin ichiro Noro, Masaru Hashimoto, Tatsuya Morozumi, Taiki Umezawa
European Journal of Organic Chemistry, 27, 33, 02 Sep. 2024
Scientific journal

Distinct regulation of two flagella by calcium during chemotaxis of male gametes in the brown alga Mutimo cylindricus (Cutleriaceae, Tilopteridales)
Taiki Umezawa
JOURNAL OF PHYCOLOGY, Apr. 2024
Scientific journal

Novel settlement inhibition oligopeptides containing β-amino acids
Taiki Umezawa, Ira Novita Sari, Erina Yoshimura, Yasuyuki Nogata
RSC Sustainability, 2024
Scientific journal

Mild Metal-Free 1,2-Dichlorination of Alkynes by NCS-PPh3-H2O System
Jianan Yuan, Nurcahyo Iman Prakoso, Tatsuya Morozumi, Taiki Umezawa
Synthesis (Germany), 56, 5, 771, 776, 15 Sep. 2023
Scientific journal

Formation pathway by by-products in methacrolein oxidation over H3PMo12O40 investigated by using 12C-labeled methacrolein
Mitsuru Kanno, Jun Hirata, Taiki Umezawa, Wataru Ninomiya, Yuichi Kamiya
Journal of the Japan Petroleum Institute, 66, 4, 128, 131, Japan Petroleum Institute, 01 Jul. 2023, [Peer-reviewed]
English, Scientific journal

Syntheses and Biological Activities of Danicalipin A Derivatives.
Taiki Umezawa, Takeshi Maeda, Takuya Akiyama, Nurcahyo Iman Prakoso, Jakia Jerin Mehjabin, Tatsufumi Okino, Fuyuhiko Matsuda
Chemistry & biodiversity, 20, 6, e202300400, Jun. 2023, [International Magazine]
English, Scientific journal, Synthesis of three derivatives of danicalipin A, tetrachloride, trisulfate and a fluorescent probe was achieved through Wittig reaction strategy. Toxicity of the derivatives against brine shrimp (Artemia salina) as also investigated to provide useful information for the biological activity; i) less chloride derivative showed similar toxicity to danicalipin A, ii) the amphiphilic property, a characteristic feature of danicalipin A, was crucial because trisulfate considerably decreased the toxicity and iii) fluorescent derivative kept brine shrimp toxicity of danicalipin A.

Scope and limitations of absolute configuration determination of allenic natural products using the CCC stretching VCD signal.
Tohru Taniguchi, Mutmainah, Shu Takimoto, Takahiro Suzuki, Soichiro Watanabe, Fuyuhiko Matsuda, Taiki Umezawa, Kenji Monde
Organic & biomolecular chemistry, 21, 3, 569, 574, Royal Society of Chemistry ({RSC}), 18 Jan. 2023, [International Magazine]
English, Scientific journal, The allene functional group in natural products isolated so far exists in a non-racemic form, but its axial chirality is difficult to elucidate. Allenes exhibit a characteristic antisymmetric CCC stretching mode at around 1950 cm-1, and their VCD properties have not been studied in detail. This work, for the first time, applied VCD spectroscopy to allenic natural products and allenic molecules with other asymmetric centers focusing on the antisymmetric CCC stretching mode. This vibrational mode yielded a negligibly weak VCD signal for several molecules, but in the presence of electron-withdrawing and/or conjugating substituents, it generated a stronger one. Its sign was found to be influenced by the nature of substituents. These findings should deepen the understanding of the VCD properties of the allene functional group and should be useful for future studies of chiral allenes.

Model Study toward Total Synthesis of Mytilipin C
Taiki Umezawa, Nurcahyo Iman Prakoso, Koichi Tsuji, Yosuke Ogura, Takumi Sato, Fuyuhiko Matsuda
Bulletin of the Chemical Society of Japan, 95, 10, 1491, 1500, The Chemical Society of Japan, 15 Oct. 2022
English, Scientific journal

Nostosin G and Spiroidesin B from the Cyanobacterium Dolichospermum sp. NIES-1697
Chin-Soon Phan, Jakia Jerin Mehjabin, Andrea Roxanne J. Anas, Masahiro Hayasaka, Reiko Onoki, Juting Wang, Taiki Umezawa, Kenji Washio, Masaaki Morikawa, Tatsufumi Okino
Journal of Natural Products, American Chemical Society (ACS), 10 Aug. 2022
Scientific journal

Enantioselective Total Synthesis of Multifidene, a Sex Pheromone of Brown Algae
Taiki Umezawa, Misaki Hara, Nana Kinoshita-Terauchi, Fuyuhiko Matsuda
Organics, 3, 3, 187, 195, MDPI AG, Jul. 2022
Scientific journal, The total synthesis of multifidene, a sex pheromone found in brown algae, is described. The synthesis features the highly enantioselective and diastereoselective addition reaction of an aldehyde to a nitroolefin in the presence of a Hayashi–Jørgensen catalyst and a Nef reaction initiated by visible light irradiation. These key reactions enabled the 11-step synthesis from commercially available compounds. The synthetic pheromones are examined with gametes.

Effective Synthesis and Antifouling Activity of Dolastatin 16 Derivatives.
Loida O Casalme, Keisuke Katayama, Yoshiki Hayakawa, Kensuke Nakamura, Arisa Yamauchi, Yasuyuki Nogata, Erina Yoshimura, Fuyuhiko Matsuda, Taiki Umezawa
Marine drugs, 20, 2, 04 Feb. 2022, [International Magazine]
English, Scientific journal, Some derivatives of dolastatin 16, a depsipeptide natural product first obtained from the sea hare Dolabella auricularia, were synthesized through second-generation synthesis of two unusual amino acids, dolaphenvaline and dolamethylleuine. The second-generation synthesis enabled derivatizations such as functionalization of the aromatic ring in dolaphenvaline. The derivatives of fragments and whole structures were evaluated for antifouling activity against the cypris larvae of Amphibalanus amphitrite. Small fragments inhibited the settlement of the cypris larvae at potent to moderate concentrations (EC50 = 0.60-4.62 μg/mL), although dolastatin 16 with a substituent on the aromatic ring (24) was much less potent than dolastatin 16.

Efficient synthesis of α,β-dichlorinated ketones from α,β-dichlorinated Weinreb amides through a simple work-up procedure.
Nurcahyo Iman Prakoso, Fuyuhiko Matsuda, Taiki Umezawa
Organic & biomolecular chemistry, 19, 36, 7822, 7826, 22 Sep. 2021, [International Magazine]
English, Scientific journal

Assignment of Absolute Configuration of Bromoallenes by Vacuum-Ultraviolet Circular Dichroism (VUVCD).
Taiki Umezawa, Nakaba Mizutani, Koichi Matsuo, Yuugo Tokunaga, Fuyuhiko Matsuda, Tatsuo Nehira
Molecules (Basel, Switzerland), 26, 5, 27 Feb. 2021, [International Magazine]
English, Scientific journal

Biosurfactants from Marine Cyanobacteria Collected in Sabah, Malaysia
Jakia Jerin Mehjabin, Liang Wei, Julie G. Petitbois, Taiki Umezawa, Fuyuhiko Matsuda, Charles S. Vairappan, Masaaki Morikawa, Tatsufumi Okino
Journal of Natural Products, 83, 6, 1925, 1930, American Chemical Society (ACS), 20 May 2020, [Peer-reviewed], [International Magazine]
English, Scientific journal

A Reliable Method to Create Adjacent Acid-Base Pair Sites on Silica through Hydrolysis of Pre-anchored Amide
Wontae Kim, Loida O. Casalme, Taiki Umezawa, Fuyuhiko Matsuda, Ryoichi Otomo, Yuichi Kamiya
Chemistry Letters, 49, 1, 71, 74, The Chemical Society of Japan, 05 Jan. 2020
Scientific journal

Neighboring Effect of Intramolecular Chlorine Atoms on Epoxide Opening Reaction by Chloride Anions.
Taiki Umezawa, Masayuki Shibata, Ryutaro Tamagawa, Fuyuhiko Matsuda
Organic letters, 21, 19, 7731, 7735, 04 Oct. 2019, [International Magazine]
English, Scientific journal

A brown algal sex pheromone reverses the sign of phototaxis by cAMP/Ca-dependent signaling in the male gametes of Mutimo cylindricus (Cutleriaceae)
Kinoshita-Terauchi, Nana, Shiba, Kogiku, Umezawa, Taiki, Matsuda, Fuyuhiko, Motomura, Taizo, Inaba, Kazuo
Journal of photochemistry and photobiology. B, Biology, 192, 113, 123, ELSEVIER SCIENCE SA, Mar. 2019, [Peer-reviewed]
English, Scientific journal, Male gametes of the brown alga Mutimo cylindricus show positive phototaxis soon after spawning in seawater but gradually change the sign of phototaxis with time. This conversion appears to need the decrease of intracellular Ca concentration. In this study, we revealed that the conversion of male gamete phototactic sign, positive to negative, was accelerated by mixing with female gametes. The supernatant after the centrifugation of female gamete suspension showed the same activity to change the phototactic sign, suggesting that a factor released from female gametes was responsible for the reaction. A known brown algal sex pheromone, ectocarpene, induced chemotaxis of male gametes of M. cylindricus. The addition of this compound induced the change of phototactic sign, clearly indicating that a sex pheromone is essential for the reversal. An inhibitor of phosphodiesterase, theophylline, inhibited the chemotaxis and phototactic sign reversion by a factor released from female gametes and ectocarpene. Measurements of cyclic nucleotides showed that the increase in intracellular concentration of cAMP, not cGMP, was parallel to the change of phototactic sign. The inhibition of phototactic s

A brown algal sex pheromone reverses the sign of phototaxis by cAMP/Ca2+-dependent signaling in the male gametes of Mutimo cylindricus (Cutleriaceae)
Kinoshita-Terauchi Nana, Shiba Kogiku, Umezawa Taiki, Matsuda Fuyuhiko, Motomura Taizo, Inaba Kazuo
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 192, 113, 123, Mar. 2019, [Peer-reviewed], [International Magazine]
English, Scientific journal

Synthesis and Structure-Activity Relationship of Omaezallene Derivatives.
Taiki Umezawa, Nurcahyo Iman Prakoso, Miho Kannaka, Yasuyuki Nogata, Erina Yoshimura, Tatsufumi Okino, Fuyuhiko Matsuda
Chemistry & biodiversity, 16, 1, e1800451, Jan. 2019, [Peer-reviewed], [International Magazine]
English, Scientific journal

Total synthesis of omaezallene toward structure determination
Taiki Umezawa
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 76, 5, 426, 429, 2018, [Peer-reviewed]
Japanese, Scientific journal

Antioxidants from the brown alga dictyopteris undulata
Momochika Kumagai, Keisuke Nishikawa, Hiroshi Matsuura, Taiki Umezawa, Fuyuhiko Matsuda, Tatsufumi Okino
Molecules, 23, 5, 2018, [Peer-reviewed], [International Magazine]
English, Scientific journal

Serinolamides and Lyngbyabellins from an Okeania sp Cyanobacterium Collected from the Red Sea
Julie G. Petitbois, Loida O. Casalme, Julius Adam V. Lopez, Walied M. Alarif, Ahmed Abdel-Lateff, Sultan S. Al-Lihaibi, Erina Yoshimura, Yasuyuki Nogata, Taiki Umezawa, Fuyuhiko Matsuda, Tatsufumi Okino
JOURNAL OF NATURAL PRODUCTS, 80, 10, 2708, 2715, Oct. 2017, [Peer-reviewed], [International Magazine]
English, Scientific journal

Total synthesis of (-)-kainic acid and (+)-allo-kainic acid through SmI2-mediated intramolecular coupling between allyl chloride and an alpha,beta-unsaturated ester
Junya Suzuki, Natsumi Miyano, Shunpei Yashiro, Taiki Umezawa, Fuyuhiko Matsuda
ORGANIC & BIOMOLECULAR CHEMISTRY, 15, 31, 6557, 6566, Aug. 2017, [Peer-reviewed], [International Magazine]
English, Scientific journal

Columbamides D and E: Chlorinated Fatty Acid Amides from the Marine Cyanobacterium Moorea bouillonii Collected in Malaysia
Julius Adam V. Lopez, Julie G. Petitbois, Charles S. Vairappan, Taiki Umezawa, Fuyuhiko Matsuda, Tatsufumi Okino
ORGANIC LETTERS, 19, 16, 4231, 4234, Aug. 2017, [Peer-reviewed], [International Magazine]
English, Scientific journal

Design, Synthesis, and Antifouling Activity of Glucosamine-Based Isocyanides
Taiki Umezawa, Yuki Hasegawa, Ira S. Novita, Junya Suzuki, Tatsuya Morozumi, Yasuyuki Nogata, Erina Yoshimura, Fuyuhiko Matsuda
MARINE DRUGS, 15, 7, Jul. 2017, [Peer-reviewed], [International Magazine]
English, Scientific journal

Total synthesis and biological activity of dolastatin 16
Loida O. Casalme, Arisa Yamauchi, Akinori Sato, Julie G. Petitbois, Yasuyuki Nogata, Erina Yoshimura, Tatsufumi Okino, Taiki Umezawa, Fuyuhiko Matsuda
ORGANIC & BIOMOLECULAR CHEMISTRY, 15, 5, 1140, 1150, Feb. 2017, [Peer-reviewed], [International Magazine]
English, Scientific journal

EFFECT OF SEX PHEROMONE ON THE SIGN OF PHOTOTAXIS IN BROWN ALGAL MALE GAMETES
Taiki Umezawa
PHYCOLOGIA, 2017
Scientific journal

Total Synthesis of Natural Antifouling Products
Taiki Umezawa, Keisuke Nishikawa, Tatsufumi Okino, Fuyuhiko Matsuda
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 74, 7, 689, 699, Jul. 2016, [Peer-reviewed]
Japanese, Scientific journal

Synthetic study on dolastatin 16: concise and scalable synthesis of two unusual amino acid units
Taiki Umezawa, Akinori Sato, Yasuto Ameda, Loida O. Casalme, Fuyuhiko Matsuda
TETRAHEDRON LETTERS, 56, 1, 168, 171, Jan. 2015, [Peer-reviewed]
English, Scientific journal

cDNA cloning and characterization of vanadium-dependent bromoperoxidases from the red alga Laurencia nipponica
Kensuke Kaneko, Kenji Washio, Taiki Umezawa, Fuyuhiko Matsuda, Masaaki Morikawa, Tatsufumi Okino
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 78, 8, 1310, 1319, Aug. 2014, [Peer-reviewed], [International Magazine]
English, Scientific journal

Recent progress toward synthesis of chlorosulfolipids: total synthesis and methodology
Taiki Umezawa, Fuyuhiko Matsuda
TETRAHEDRON LETTERS, 55, 19, 3003, 3012, May 2014, [Peer-reviewed]
English, Scientific journal

Omaezallene from Red Alga Laurencia sp.: Structure Elucidation, Total Synthesis, and Antifouling Activity
Taiki Umezawa, Yuko Oguri, Hiroshi Matsuura, Shohei Yamazaki, Masahiro Suzuki, Erina Yoshimura, Takeshi Furuta, Yasuyuki Nogata, Yukihiko Serisawa, Kazuyo Matsuyama-Serisawa, Tsuyoshi Abe, Fuyuhiko Matsuda, Minoru Suzuki, Tatsufumi Okino
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 53, 15, 3909, 3912, Apr. 2014, [Peer-reviewed], [International Magazine]
English, Scientific journal

Bromoperoxidases from Laurencia species
Kaneko Kensuke, Washio Kenji, Umezawa Taiki, Kobayashi Daiki, Tang Xiaorong, Matsuda Fuyuhiko, Morikawa Masaaki, Okino Tatsufumi
Symposium on the Chemistry of Natural Products, symposium papers, 56, Poster53, Symposium on the Chemistry of Natural Products Steering Committee, 2014
Japanese, The genus of red alga Laurencia is one of the richest producers of halogenated compounds (mostly brominated) ³⁾. Murai et al ⁴⁾ and Butler et al ⁹⁾ showed enzymatic bromination of Laurencia C₁₅acetogenins including laurencin (1) ^1,2)and sesquiterpenoids snyderols using partially purified bromoperoxidase (BPO) from L. nipponica and vanadium-dependent BPO (VBPO) from a mixture of red algae including L. pacifica. However, since the lack of information of sequences, the structural information and biochemical aspects of BPO from L. nipponica and VBPO from L. pacifica remains unknown. Here, we report cDNA cloning of VBPOs from L. nipponicaand in vitro enzymatic bromination of putative biosynthetic precursors using recombinant enzymes.

Two VBPOs (LnVBPO1 and LnVBPO2) were cloned from L. nipponica and recombinant LnVBPOs were prepared. Recombinant LnVBPOs were subjected to enzyme activity assay. A general substrate, monochlorodimedone (MCD), was utilized for K_m determination for H₂O₂ and , essential for bromination of organic substrate. K_m for H₂O₂was 0.03 mM in both LnVBPOs, K_m for were 0.53 mM for LnVBPO1 and 0.35 mM for LnVBPO2, respectively. A derivative of putative precursor of laurencin (1), TMS-capped (3E, 6R, 7R)-laurediol (4) was subjected to LnVBPOs enzymatic bromination and gave similar MS/MS spectrum of deacetylaurencin (3). Since the compound 3 is considered to be the final precursor of 1, it is suggested that VBPO catalyzes bromination in Laurenciametabolites.

We also cloned VBPOs from other Laurencia spp. which produce brominated sesquiterpenoids (L. okamurae) and triterpenoids (L. saitoi). We will discuss in vitro enzymatic bromination of these two LaurenciaVBPOs.

Total Synthesis of Omaezallene and Determination of its Absolute Stereochemistries
Umezawa Taiki, Yamazaki Shohei, Oguri Yuko, Matsuura Hiroshi, Suzuki Masahiro, Okino Tatsufumi, Matsuda Fuyuhiko
Symposium on the Chemistry of Natural Products, symposium papers, 55, Oral24, Symposium on the Chemistry of Natural Products Steering Committee, 2013
Japanese, Omaezallene (1) was isolated from Laurencia sp. and showed strong antifouling activity against the larvae of the barnacle amphitrite. Although organotin compounds, such as tributyltin (TBT), had been widely used as a fouling inhibitor, the use of TBT was prohibited by IMO in 2008 due to its toxicity. Therefore, the development of the potent nontoxic fouling inhibitor is desired strongly, and 1 is expected to be a lead compound as the fouling inhibitor. Although the relative and absolute structure of 1 was assumed using 1D- and 2D-NMR experiments, the relative configurations have not been determined completely, especially the configuration at C9 position. To determine the relative configurations as well as the absolute configuration, the synthetic study toward 1 was started.

The synthesis commenced with the known aldehyde 3, derived from D-glucose in 5 steps, which was transformed into the unsaturated ester 8 with E geometry. The ester 8 was next converted to the hemiacetal 10 in 3 steps. The treatment of ethynylmagnesium chloride to 10 afforded the desired propargy alcohol 4 as a major diastereomer. Cyclization of 4 with NBS furnished the construction of the two contiguous stereocenters to give bromoether 11 in a highly stereoselective manner, which was then derived to the aldehyde 6 in 4 steps. 6 was successfully converted to 1via cyanohydrin formation, HWE reaction, and Wittig reaction involving in-situ bromination of reagent. By the total synthesis, the absolute configuration of 1was unambiguously determined as shown in scheme 5.

Confirmation of the Configuration of 10-Isothiocyanato-4-cadinene Diastereomers through Synthesis
Keisuke Nishikawa, Taiki Umezawa, Mary J. Garson, Fuyuhiko Matsuda
JOURNAL OF NATURAL PRODUCTS, 75, 12, 2232, 2235, Dec. 2012, [Peer-reviewed], [International Magazine]
English, Scientific journal

P-11 Three-component Coupling Reaction with Aldehyde, Acyl Fluoride and Trimethylsilylmethylphosphonate(Poster Presentation)
Umezawa Taiki, Seino Tomoya, Matsuda Fuyuhiko
Symposium on the Chemistry of Natural Products, symposium papers, 54, 297, 302, Symposium on the chemistry of natural products, 01 Sep. 2012
Japanese, Horner-Wadsworth-Emmons reaction (HWE reaction) is known as a reliable and powerful method for carbon-carbon bond formation by coupling between β-ketophosphonate and aldehyde to give α,β-unsaturated compound with high stereoselectivity. In general, the β-ketophosphonate used as the HWE reaction precursor is needed to be synthesized from a readily accessible material. However, these procedures sometimes encounter troubles in purification due to its high polarity or side products. To avoid these problems, we planned one-pot synthesis of the α,β-unsaturated ketone with aldehyde, acyl fluoride and trimethylsilylmethylphosphonate through HWE reaction according to the sequential reaction illustrated in Scheme 1. The reaction conditions were optimized by examining bases, reaction time, and equivalent of reagents as shown in Table 1. With the optimized conditions (Table 1. Entry 7), wide variety of substrates (aldehyde, acyl fluoride, and phosphonate) bearing various functional groups were coupled to give α,β-unsaturated ketone in high yields with E geometry. (Table 2) Z-α,β-Unsaturated ketones were also prepared with high stereoselectivity by using one-pot procedure. (Table 3)

Thrombin Inhibitors from the Freshwater Cyanobacterium Anabaena compacta
Andrea Roxanne J. Anas, Takaya Kisugi, Taiki Umezawa, Fuyuhiko Matsuda, Marc R. Campitelli, Ronald J. Quinn, Tatsufumi Okino
JOURNAL OF NATURAL PRODUCTS, 75, 9, 1546, 1552, Sep. 2012, [Peer-reviewed], [International Magazine]
English, Scientific journal

Novel One-pot Three-component Coupling Reaction with Trimethylsilylmethylphosphonate, Acyl Fluoride, and Aldehyde through the Horner-Wadsworth-Emmons Reaction
Taiki Umezawa, Tomoya Seino, Fuyuhiko Matsuda
ORGANIC LETTERS, 14, 16, 4206, 4209, Aug. 2012, [Peer-reviewed], [International Magazine]
English, Scientific journal

Synthesis and Biological Activity of Kalkitoxin and its Analogues
Taiki Umezawa, Manabu Sueda, Takao Kamura, Teppei Kawahara, Xuerong Han, Tatsufumi Okino, Fuyuhiko Matsuda
JOURNAL OF ORGANIC CHEMISTRY, 77, 1, 357, 370, Jan. 2012, [Peer-reviewed], [International Magazine]
English, Scientific journal

Asymmetric Total Synthesis of Danicalipin A
Umezawa Taiki, Shibata Masayuki, Matsuda Fuyuhiko
Symposium on the Chemistry of Natural Products, symposium papers, 52, 1, 6, Symposium on the chemistry of natural products, 01 Sep. 2010
Japanese, Danicalipin A (1), a major component of chlorosulfolipids (CSLs) from Ochromonas danica, was first isolated more than four decades ago along wigh its congeners 2-6. Although the planar structure of 1 was reorted in 1973, the absolute and relative stereochemistries of 1 have not been determined until 2009; total synthesis by Vanderwal and NMR analysis of natural sample by Okino. Due to the unprecedent structure of CSLs, CSLs have attracted much attention of synthetic chemists and total syntheses of 1, 7, and 8 were achieved by three groups. In this presentation, asymmetric total synthesis of Danicalipin A (1) will be described. The synthesis commenced with the known optically active epoxide 14, derived via Sharpless-Katsuki asymmetric epoxidation, which was transformed into the α,β-unsaturated ester 15. (Scheme 2) At this stage, the enantiomeric excess of 15 was enhanced from 85% ee to >99% ee by recrystallization. Four transformations involving regioselective epoxy opening reaction gave the aldehyde 13. After diastereoselective α-chlorination of 13 with 19, the aldehyde 10 was synthesized in 2 steps. Wittig reaction between 10 and the phosphonium salt 11, derived from the known aldehyde 12, afforded the alkene 24. E-olefin for the trans-dichloride at C15 and 16 was installed by Wiitg olefination, furnishing the α,β-unsaturated ester 26. After introduction of n-hexyl group from ester, trans addition of chlorine equivalent into E-olefin at 80℃ gave the adduct 29, which was successfully converted to Danicalipin A.

Synthesis and Biological Activity of Kalkitoxin and its Analogues
Umezawa Taiki, Kamura Takao, Kawahara Teppei, Sueda Manabu, Kan Setsuyo, Okino Tatsufumi, Matsuda Fuyuhiko
Symposium on the Chemistry of Natural Products, symposium papers, 51, 329, 334, Symposium on the chemistry of natural products, 01 Sep. 2009
Japanese, Kalkitoxin (1) was isolated from cyanobacterium Lyngbya majuscule in the Caribbean Sea. It is reported that 1 posssesses some intersting biological activities. For example, 1 shows a strong ichtyotoxic activity toward the common gold fish and brine shrimp. Also, kalkitoxin has a strong neurotoxicity (LC_<50>=3.86nM) in cerebellar granule neouron (CGN) as an inhibitor N-methyl-D-aspartate (NMDA) receptor antagonists and is a highly potent blocker of the voltage-depending sodium channel in mouse neuro-2a cells (EC_<50>=1nM). We have been attracted by the structure-activity relationship of kalkitoxins. In present paper, we describe the synthesis of kalkitoxin and its analogues (epimer and demethylated kalkitoxins (nor form) and their biological activity with brine shrimp. The synthesis was started from 15, which was converted to α,β-unsaturaed imide 14 with phosphonate 17. 1,4-Addition reaction to 14 with methyl curprate gave imide 18 as 10 : 1 mixture of diastereomers. The imide 18 was transformed into second 1,4-addition precursor 11 in 9 steps. The conjugate addition reaction of 11 proceeded smoothly to give imide 26 as a single diastereomer, which was derived to 1 via condensation with amine 10, synthesize without racemization by novel method, and highly efficient thiazoline formation with TiCl_4. Kalkitoxin analogues 2-7 were synthesized in the similar manner by simply changing the chiral auxiliary or chiral building block. Finally, the biological activity with 1-7 was evaluated as LC_<50> toward brine shrimp.

P-80 Total Synthesis of Isocyanocadinene(Poster Presentation)
Nishikawa Keisuke, Shirokura Yousuke, Nakahara Hiroshi, Umezawa Taiki, Matsuda Fuyuhiko
Symposium on the Chemistry of Natural Products, symposium papers, 50, 777, 782, Symposium on the chemistry of natural products, 01 Sep. 2008
Japanese, 10-Isocyano-4-cadinene (1), a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae by Okino et al., exhibits potent antifouling activity against the larvae of the barnacle Balanus amphitrite (EC_<50> 0.14μg/mL). 10-Isocyano-4-cadinene (1) is expected to be new nontoxic antifouling agents. Furthermore, the absolute stereochemistry of 1 has not been determined. To access these issues, we started the enantioselective total synthesis toward 1. The synthesis toward 1 was commenced with known imide 6, which was converted into dieneacetate 5c in 9 steps. The Diels-Alder reaction between 5c and methyl acrylate with MeAlCl_2 afforded cyclohexene 11c as a mixture of four diasereomers. This mixture was epimerized to two isomers, desired carboxylic acid 12 as a major product and ester 13, by the treatment of NaOMe followed by selective hydrolysis with 1N HCl in one-pot. Carboxylic acid 12 was transformed into aldehyde 14, which was cyclized by SmI_2-induced Barbier-type reaction to give alcohol 15. To introduce the functional groups at C10, homologation of 15 with TosMIC afforded aldehyde 16, which was treated with t-BuOK and 21 to give MPM ether 22 in stereoselective fashion. Wolff-Kishner reaction followed by Curtis rearrangement of 24 gave isocyanate 25, C10 was fully functionalized. Total synthesis was completed by reduction of isocyano group with NaBH_4 and dehydration with POCl_3. The absolute configuration of 1 was determined as (1R, 6R, 7S, 10R) by the comparison with the optical rotation between natural and synthetic samples.

ELASTIC AND INELASTIC BEHAVIORS OF ROCK MASSES IN THE LOAD-DISPLACEMENT RELATION OBTAINED THROUGH BOREHOLE JACKING
Taiki Umezawa
EUROCK 93, LISBOA, PORTUGAL - PROCEEDINGS : SAFETY AND ENVIRONMENTAL ISSUES IN ROCK ENGINEERING, VOL 1, 1993
Scientific journal

A STUDY ON THE OXIDATION-STATE OF BI-LAYERED ANODIZED FILMS
Taiki Umezawa
IEICE TRANSACTIONS ON COMMUNICATIONS ELECTRONICS INFORMATION AND SYSTEMS, 1991
Scientific journal

Study on Development of Antifouling Compounds Inspired by Defense System of Marine Organims
梅澤大樹, 月刊ファインケミカル, 54, 5, 2025

1,2-ジブロモアルケンからのアルキン合成
奥村日向, 諸角達也, 梅澤大樹, 化学系学協会北海道支部冬季研究発表会(Web), 2024, 2024

Formation Pathway of By-products in Methacrolein Oxidation over H₃PMo₁₂O₄₀ Investigated by Using ¹³C-Labeled Methacrolein
菅野充, 平田純, 梅澤大樹, 二宮航, 神谷裕一, Journal of the Japan Petroleum Institute (Web), 66, 4, 2023

Attempts toward Creation of Antifouling Organic Compounds: Effective Synthesis by Incorporation of Antifouling Unit
梅澤大樹, 化学と生物, 61, 7, 2023

¹³C同位体標識基質を用いたH₃PMo₁₂O₄₀上でのメタクロレイン酸化反応機構の解析
菅野充, 平田純, 梅澤大樹, 二宮航, 神谷裕一, 触媒討論会討論会A予稿集(CD-ROM), 130th, 2022

Synthetic Study on multifidene, sex pheromone of blown algae
原美咲, 松田冬彦, 梅澤大樹, 天然有機化合物討論会講演要旨集(Web), 62nd, 2020

Synthetic Study on Dolastatin 16 Derivatives
早川嘉樹, 中村謙介, CASALME Loida O., 梅澤大樹, 松田冬彦, 天然有機化合物討論会講演要旨集(Web), 60th, 2018

有機合成から着生問題へのアプローチ:着生機構解明のためのプローブ化を志向した着生阻害天然物の合成研究
梅澤大樹, Sessile Organisms, 35, 1, 2018

A study on synthesis of antifouling natural products and their derivatives
梅澤大樹, 松田冬彦, Sessile Organisms, 35, 2, 2018

マリンバイオマス由来付着阻害剤の構造―活性相関研究
梅澤大樹, 長谷川裕己, SARI Ira Novita, 鈴木惇也, 諸角達也, 野方靖行, 吉村えり奈, 松田冬彦, マリンバイオテクノロジー学会大会講演要旨集, 19th, 80, 03 Jun. 2017
Japanese

グルコサミン由来の付着阻害剤の合成と付着阻害活性
梅澤大樹, 長谷川裕己, SARI Ira Novita, 鈴木惇也, 諸角達也, 松田冬彦, 野方靖行, 吉村えり奈, Sessile Organisms, 34, 2, 2017

Synthetic study on dolastatin 16: concise and scalable synthesis of two unusual amino acid units
Taiki Umezawa, Akinori Sato, Yasuto Ameda, Loida O. Casalme, Fuyuhiko Matsuda, TETRAHEDRON LETTERS, 56, 1, 168, 171, Jan. 2015
English

Recent progress toward synthesis of chlorosulfolipids: total synthesis and methodology
Taiki Umezawa, Fuyuhiko Matsuda, TETRAHEDRON LETTERS, 55, 19, 3003, 3012, May 2014
English

紅藻ウラソゾLaurencia nipponica由来バナジウム依存型ブロモペルオキシダーゼの性状解析
KANEKO KENSUKE, WASHIO KENJI, UMEZAWA DAIKI, MATSUDA FUYUHIKO, MORIKAWA MASAAKI, OKINO TATSUFUMI, 日本水産学会大会講演要旨集, 2014, 119, 27 Mar. 2014
Japanese

Danicalipin A誘導体の合成研究
MAEDA TAKESHI, UMEZAWA TAIKI, MATSUDA FUYUHIKO, 日本化学会講演予稿集, 94th, 4, 1492, 12 Mar. 2014
Japanese

Dolastatin16の全合成研究
SATO AKINORI, UMEZAWA TAIKI, MATSUDA FUYUHIKO, 日本化学会講演予稿集, 94th, 4, 1468, 12 Mar. 2014
Japanese

効率的ビニグロールの合成研究
UMEZAWA DAIKI, 上原記念生命科学財団研究報告集(CD-ROM), 27, ROMBUNNO.11, 4, 10 Dec. 2013
上原記念生命科学財団, Japanese

紅藻ウラソゾLaurencia nipponica由来バナジウム依存型ブロモペルオキシダーゼの性状解析
KANEKO KENSUKE, WASHIO KENJI, UMEZAWA DAIKI, MATSUDA FUYUHIKO, MORIKAWA MASAAKI, OKINO TATSUFUMI, マリンバイオテクノロジー学会大会講演要旨集, 15th, 68, 01 Jun. 2013
Japanese

Mytilipin Cの全合成研究
UMEZAWA TAIKI, SEINO TOMOYA, MATSUDA FUYUHIKO, 日本化学会講演予稿集, 93rd, 4, 1202, 08 Mar. 2013
Japanese

アルデヒド,酸フッ化物,トリメチルシリルメチルホスホネートの3成分カップリング反応
UMEZAWA TAIKI, SEINO TOMOYA, MATSUDA FUYUHIKO, 日本化学会講演予稿集, 92nd, 4, 1156, 09 Mar. 2012
Japanese

Stereoselective Total Syntheses of Chlorosulfolipids
Taiki Umezawa, Fuyuhiko Matsuda, JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 69, 10, 1122, 1133, Oct. 2011
Japanese, Book review

Stereoselective total syntheses of chlorosulfolipids
Taiki Umezawa, Fuyuhiko Matsuda, Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 69, 10, 1122, 1133, Oct. 2011
Japanese, Book review

オマエザレンの全合成
UMEZAWA TAIKI, SUZUKI MASAHIRO, OGURI YUKO, MATSUURA HIROSHI, OKINO TATSUFUMI, MATSUDA FUYUHIKO, 天然有機化合物討論会講演要旨集, 53rd, 637, 642, 02 Sep. 2011
Japanese

支部発 話題欄 1 天然有機化合物の化学 含ハロゲン化合物の全合成
UMEZAWA TAIKI, 化学と工業, 64, 9, 688, 689, 01 Sep. 2011
Japanese

Total Synthesis of 10-Isocyano-4-cadinene and Its Stereoisomers and Evaluations of Antifouling Activities
Keisuke Nishikawa, Hiroshi Nakahara, Yousuke Shirokura, Yasuyuki Nogata, Erina Yoshimura, Taiki Umezawa, Tatsufumi Okino, Fuyuhiko Matsuda, JOURNAL OF ORGANIC CHEMISTRY, 76, 16, 6558, 6573, Aug. 2011, [International Magazine]
English

Asymmetric Total Synthesis of Danicalipin A and Evaluation of Biological Activity
Taiki Umezawa, Masayuki Shibata, Kensuke Kaneko, Tatsufumi Okino, Fuyuhiko Matsuda, ORGANIC LETTERS, 13, 5, 904, 907, Mar. 2011, [International Magazine]
English

Synthesis of C-13-Labeled 5,6,11-Trideoxytetrodotoxin
Taiki Umezawa, Tetsuro Shinada, Yasufumi Ohfune, CHEMISTRY LETTERS, 39, 12, 1281, 1282, Dec. 2010
English

Mild and Catalytic Transesterification Reaction Using K2HPO4 for the Synthesis of Methyl Esters
Tetsuro Shinada, Makoto Hamada, Kota Miyoshi, Masato Higashino, Taiki Umezawa, Yasufumi Ohfune, SYNLETT, 14, 2141, 2145, Sep. 2010
English

Synthesis of the QRSTU Domain of Maitotoxin and Its 85-epi- and 86-epi-Diastereoisomers
K. C. Nicolaou, Christine F. Gelin, Jae Hong Seo, Zhihong Huang, Taiki Umezawa, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 132, 28, 9900, 9907, Jul. 2010
English

Isocyanocadinene及びその立体異性体の合成とそれらの着生阻害活性の評価
西川慶祐, 代蔵陽介, 野方靖行, 吉村えり奈, 梅澤大樹, 沖野龍文, 松田冬彦, 日本化学会講演予稿集, 90th, 4, 1043, 12 Mar. 2010
Japanese

Total Synthesis of 10-Isocyano-4-cadinene and Determination of Its Absolute Configuration
Keisuke Nishikawa, Hiroshi Nakahara, Yousuke Shirokura, Yasuyuki Nogata, Erina Yoshimura, Taiki Umezawa, Tatsufumi Okino, Fuyuhiko Matsuda, ORGANIC LETTERS, 12, 5, 904, 907, Mar. 2010
English

テルペン類の全合成 : 骨格形成法の新展開
松田 冬彦, 梅澤 大樹, ファルマシア, 44, 10, 959, 964, 01 Oct. 2008
公益社団法人日本薬学会, Japanese

Chemical synthesis of the GHIJKLMNO ring system of maitotoxin
K. C. Nicolaou, Michael O. Frederick, Antonio C. B. Burtoloso, Ross M. Denton, Fatima Rivas, Kevin P. Cole, Robert J. Aversa, Romelo Gibe, Taiki Umezawa, Takahiro Suzuki, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 130, 23, 7466, 7476, Jun. 2008
English

Total synthesis of (-)-5,6,11-trideoxytetrodotoxin and its 4-epimer
Taiki Umezawa, Toshihiro Hayashi, Hiroshi Sakai, Hidetoshi Teramoto, Takeshi Yoshikawa, Masashi Izumida, Yoshinori Tamatani, Tadashi Hirose, Yasufumi Ohfune, Tetsuro Shinada, ORGANIC LETTERS, 8, 21, 4971, 4974, Oct. 2006
English

P-107 TOTAL SYNTHESIS OF 5,6,11-TRIDEOXYTETRODOTOXIN
Shinada Tetsuro, Umezawa Taiki, Hayashi Toshihiro, Sakai Hiroshi, Kawakami Tadashi, Teramoto Hidetoshi, Yoshikawa Takeshi, Izumida Masashi, Tamatani Yoshinori, Hirose Tadashi, Ohfune Yasufumi, International Symposium on the Chemistry of Natural Products, 2006, "P, 107", 23 Jul. 2006
天然有機化合物討論会, English

P-216 SYNTHESIS OF STELLETTADINE A BY NOVEL METHOD FOR THE SYNTHESIS OF N-ACYL-N'-SUBSTITUTED GUANIDINES
Kozuma Hayato, Umezawa Taiki, Ando Takeshi, Shinada Tetsuro, Ohfune Yasufumi, International Symposium on the Chemistry of Natural Products, 2006, "P, 216", 23 Jul. 2006
天然有機化合物討論会, English

On the stereoselectivity of asymmetric strecker synthesis in a cyclohexane system: Synthesis of optically active cis- and trans-1-amino-2-hydroxycyclohexane-1-carboxylic acids
Tetsuro Shinada, Tadashi Kawakami, Hiroshi Sakai, Hiromi Matsuda, Taiki Umezawa, Masaki Kawasaki, Kosuke Namba, Yasufumi Ohfune, BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 79, 5, 768, 774, May 2006
English

On the stereoselectivity of asymmetric strecker synthesis in a cyclohexane system: Synthesis of optically active cis- and trans-1-amino-2-hydroxycyclohexane-1-carboxylic acids
Tetsuro Shinada, Tadashi Kawakami, Hiroshi Sakai, Hiromi Matsuda, Taiki Umezawa, Masaki Kawasaki, Kosuke Namba, Yasufumi Ohfune, BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 79, 5, 768, 774, May 2006
English

A new entry for the synthesis of N-acyl-N '-substituted guanidines
T Shinada, T Umezawa, T Ando, H Kozuma, Y Ohfune, TETRAHEDRON LETTERS, 47, 12, 1945, 1947, Mar. 2006
English

14 Total Synthesis of 5,6,11-Trideoxytetrodotoxin
Umezawa Taiki, Shinada Tetsuro, Ohfune Yasufumi, Symposium on the Chemistry of Natural Products, symposium papers, 47, 0, 77, 82, 2005
Tetrodotoxin (TTX) is a toxic principle of puffer fish poisoning. TTX is a useful biological tool because of its specificity for blocking voltage-dependent sodium channels. 5,6,11-Trideoxy TTX (1), one of the congeners of TTX, has also been isolated from ovaries of puffers, Fugu poecilonotus, by Yasumoto et al. in 1995 and received significant interests in view of biosynthetic relationship with TTX. Synthetic studies of TTX and its congeners have been extensive due to their biological activities as well as their molecular complexity consisting of a quaternary carbon center attached to an amino group, concomitant polyol system, a cyclic guanidine containing an aminal, and an ortho acid for TTX or a δ-lactone for some of the congeners. In this report, we wish to describe the first total synthesis of 5,6,11-trideoxy TTX (1) and its 4-epimer 2. The synthesis was commenced with the known triol 7, prepared from (-)-quinic acid in 4 steps, which was converted to Strecker precursor 6 in 6 steps. 6 was subjected to an asymmetric transferring Strecker synthesis for the diastereoselective construction of a quaternary carbon center involving an amino group at C8a. Installation of a hydroxy group to C7 was accomplished by the Mislow-Evans rearrangement to give 20. Initial hydrogenation of 20 for the introduction of β-methyl group at C6 and subsequent pyrrolidine ring opening via lactam 24 gave alcohol 25. The hydroxyethyl group of 25 was transformed to a vinyl group in 3 steps to give 26. Inversion of the hydroxy group at C7 was performed by oxidation to a diketone followed by diastereoselective reduction to give cis-diol 4, This was converted to aldehyde 28, which, upon treatment with TMSCN in the presence of Et_3N, gave a cyanohydrin as an inseparable mixture of diastereomers. The mixture was guanidylated to give 29. Ozonolysis of the desired (9S)-29 followed by exposure to 20% TFA afforded a mixture of 5,6,11-trideoxyTTX (1), and its 4-epimer 2 and anhydro derivative 31. Thus, the total syntheses of 1 and 2 were accomplished., 天然有機化合物討論会実行委員会, Japanese

Apr. 2021 - Present
日本農芸化学会　　　　　　　　　　　　　　　

若手研究者のための有機合成セミナー　　　　　　　　　　　　　　　
2008

Development of 1,2-thioalcohol unit from nitro group and application to total synthesis
Grants-in-Aid for Scientific Research
01 Apr. 2025 - 31 Mar. 2028
梅澤 大樹
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (C), Hokkaido University, 25K08650

環境にやさしい付着阻害剤の開発を指向した天然物誘導体合成と付着阻害メカニズム解明　　　　　　　　　　　　　　　
基盤研究（B)
Apr. 2018 - Mar. 2022
梅澤 大樹
科研費, Principal investigator, Competitive research funding

Construction of active sites composed of multi-functional groups with precisely controlled distance by use of decomposition reaction
Grants-in-Aid for Scientific Research
28 Jun. 2019 - 31 Mar. 2021
Kamiya Yuichi
Adjacent acid-base pair sites, which were consisted of carboxyl and amine groups, were constructed on silica surface by hydrolysis of an amide compound, which were anchored on the silica in advance. It was found that this catalyst showed extremely high catalytic activity for cross-aldol condensation of 4-nitrobenzaldehyde with acetone. The acid-base pair sites that were three methylene groups away from each other, which were constructed using an diamide compound that contains three methylene groups in the structure, showed less activity for the reaction that the catalyst with adjacent acid-base pair sites, demonstrating that the distance between acid and base functional groups was important factor for the reaction.
Japan Society for the Promotion of Science, Grant-in-Aid for Challenging Research (Exploratory), Hokkaido University, 19K22074

Chemical Biology of Halogenated Antifouling Compounds
Grants-in-Aid for Scientific Research
01 Apr. 2016 - 31 Mar. 2020
Okino Tatsufumi
Reaction condition of vanadium-dependent bromoperoxidase from the red alga Laurencia saitoi was optimized to propose its products by MS. Chlorinated compounds were isolated from marine cyanobacteria.
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Hokkaido University, 16H04975

海洋生物の防御機能を模倣したバイオマス循環型船底付着阻害剤の合成的探索研究　　　　　　　　　　　　　　　
環境総合研究推進費
Apr. 2016 - Mar. 2018
梅澤 大樹
環境省, Principal investigator, Competitive research funding

Biosynthetic enzymes of antifouling halogenated compounds
Grants-in-Aid for Scientific Research
01 Apr. 2012 - 31 Mar. 2016
Okino Tatsufumi, MATSUDA Fuyuhiko, UMEZAWA Taiki, NOGATA Yasuyuki, WASHIO Kenji
Vanadium dependent bromoperoxidase (VBPO) was cloned from the red alga Laurencia nipponica which produces a halogenated compound, laurencin. The enzyme catalyzed cyclization and bromination of a precursor of laurencin. Bromination activity of recombinant enzyme was investigated. A similar type of VBPO was cloned from L. okamurae which produces a halogenated sesquiterpenoid, laurinterol. The recombinant enzyme showed bromination activity. In addition, another type of VBPO was cloned from L. saitoi which produces a halogenated triterpenoid. Its properties were investigated by using its recombinant protein. The structure of bromoallene containing C15 compound, omaezallene was reported. Its totaly syntehsis was successfully achieved.
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Hokkaido University, 24380112

Synthetic study on fluorecent probe of antifouling natural products toward elucidation of molecular mechanism
Grants-in-Aid for Scientific Research
2015 - 2016
Umezawa Taiki
This study aims syntheses of fluorescent probe of antifouling natural products. As lead compounds for antifouling materials, omaezallene (brominated compound) and dolastatin 16 (cyclic peptide) are selected becuase these exhibit strong antifouling activity along with very low toxicity toward cypris larvae of Amphibalanus amphitrite. Elucidation of molecular mechanism of antifouling activity expects the development of ideal antifouling material.
Syntheses of omaezallene derivatives was achieved, which includes fluorescent derivative. A new synthetic pathway to dolastatin 16 and the antifouling activity of synthetic sample were revealed. Functionalization method toward fluorescent compound was also developed.
Japan Society for the Promotion of Science, Grant-in-Aid for Young Scientists (B), Hokkaido University, Principal investigator, Competitive research funding, 15K16551

Synthetic Study on Chlorosulfolipid toward elucidation of toxicity
Grants-in-Aid for Scientific Research(若手研究(B))
2011 - 2012
Taiki UMEZAWA
According to the plan, the synthesis of two fragments for the chlorosulfolipid and a coupling reaction conditions with the fragments were examined. As a results of the examinations, the efficient synthesis of one fragment was developed, and a new synthetic method for the synthesis of another fragment was established. The method is used for the synthesis of, -unsaturated ketone with aldehyde, trimethylsilylmethyl phosphonate, and acyl fluoride in one step, and published from a journal, Organic Letters. Synthesis of chlorosulfolipid is currently underway using the method.
Ministry of Education, Culture, Sports, Science and Technology, 若手研究(B), 北海道大学, Principal investigator, Competitive research funding, 23710245

海洋付着生物に対する付着阻害作用を有するオリゴペプチド　　　　　　　　　　　　　　　
Patent right
特願P2023-075-JP01, 06 Oct. 2023

フジツボ付着、殺さず防ぐ 新化合物、船底塗料へ応用も 北大など　　　　　　　　　　　　　　　
06 Mar. 2025
Yahoo Japan
https://news.yahoo.co.jp/articles/fa5216f764e42d4269736586dc2cef8ca6d0a7a4, [Internet]

フジツボ付着、殺さず防ぐ 新化合物、船底塗料へ応用も―北大など　　　　　　　　　　　　　　　
06 Mar. 2025
時事通信
https://www.jiji.com/jc/article?k=2025030600145&g=soc, [Internet]

船底へのフジツボ付着、アミノ酸の鎖で抑制 北大など　　　　　　　　　　　　　　　
09 Feb. 2025
日本経済新聞
[Paper]

フジツボの付着防ぐ新化合物開発 アメフラシ類がもつ物質がヒントに　　　　　　　　　　　　　　　
06 Feb. 2025
朝日新聞
[Paper]