SEARCH

Search Details

Suzuki Takahiro

Faculty of Science　Chemistry　Organic and Biological ChemistryAssociate Professor

Researcher basic information

■ Degree
  • 理学（博士）, 早稲田大学
■ URL
researchmap URLホームページURL■ Various IDs
Researcher number
  • 80367052
J-Global ID■ Research Keywords and Fields
Research Keyword
  • 合成化学
  • 有機化学
Research Field
  • Nanotechnology/Materials, Synthetic organic chemistry, 天然物合成、反応開発
  • Life Science, Bioorganic chemistry
  • Nanotechnology/Materials, Structural organic chemistry and physical organic chemistry
  • Life Science, Pharmaceutical chemistry and drug development sciences
■ Educational Organization

Career

■ Career
Career
  • Mar. 2014 - Present
    Hokkaido University, 大学院理学研究院 化学部門, Associate Professor
  • Apr. 2013 - Feb. 2014
    Waseda University, 理工学術院先進理工学部応用化学科, 助教
  • Apr. 2009 - Mar. 2013
    Tokyo University of Science, Faculty of Pharmaceutical Sciences, 助教
  • Apr. 2003 - Mar. 2005
    Waseda University, Faculty of Science and Engineering, 助手
Committee Memberships
  • Apr. 2014 - Mar. 2016
    有機合成化学協会, 編集協力委員, Society

Research activity information

■ Awards
  • Jan. 2018, 日本化学会北海道支部, 日本化学会北海道支部奨励賞
    特異な構造の天然物の全合成と拡散的研究展開
    鈴木孝洋
  • Oct. 2016, Asian Core Program Lectureship Award from HongKong
    鈴木孝洋, International society
  • Oct. 2016, Asian Core Program Lectureship Award from China
    鈴木孝洋, International society
■ Papers
■ Other Activities and Achievements
  • (+)-コリアミルチンの全合成
    池内和忠; 原口翔太; 藤井りょう; 山田英俊; 鈴木孝洋; 谷野圭持, 次世代を担う有機化学シンポジウム講演要旨集, 21st, 2023
  • A Novel Synthetic Method for Bicyclo[2.2.2]octanes from Pyridazines Using An Intramolecular Diels-Alder Cascade
    今井隆史; 鈴木孝洋; 谷野圭持, 複素環化学討論会講演要旨集, 50th, 2021
  • Improved synthetic study of atropurpuran
    古山岳史; 中西健太; 鈴木孝洋; 小林進; 谷野圭持, 日本化学会春季年会講演予稿集(CD-ROM), 100th, 2020
  • ラジカル環化反応を利用したkamebaninの全合成
    池田航; 菅野彩夏; 鈴木孝洋; 谷野圭持, 有機合成シンポジウム講演予稿集, 116th, 2019
  • 付加環化反応を基盤とした特異な環構造を有するテルペノイドの全合成研究
    鈴木孝洋, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 61st, 2017
  • Total Synthesis of Atropurpuran
    鈴木孝洋; 鈴木孝洋; 中西健太; 小林進; 谷野圭持, 天然有機化合物討論会講演要旨集(Web), 59th, 2017
  • アイボレノイドAの全合成研究
    堀口耕作; 鈴木孝洋; 谷野圭持, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 60th, 2016
  • 連続的環化反応を利用したent-カウレン類の合成研究
    菅野彩夏; 鈴木孝洋; 谷野圭持, 香料・テルペンおよび精油化学に関する討論会講演要旨集, 60th, 2016
  • DNAポリメラーゼYファミリー阻害剤ペニシリオール類の合成研究
    遠藤正伍; 黒澤敦; 志村聡美; 竹内倫文; 鈴木孝洋; 紙透伸治; 小林進; 菅原二三男, 日本農芸化学会大会講演要旨集(Web), 2014, 2014
  • 抗ウイルス活性を有する新規環状デプシペプチドMA026の合成研究と標的分子の探索
    志村聡美; 中嶋翔; 中嶋翔; 藤井俊孝; 池田健太郎; IZAGUIRRE-CARBONELL Jesus; 石間正浩; 竹内倫文; 紙透伸治; 鈴木孝洋; 倉持幸司; 渡士幸一; 渡士幸一; 小林進; 菅原二三男, 日本農芸化学会大会講演要旨集(Web), 2014, 2014
  • Total Synthesis and Phage Display Screening to identify the target of MA026, a Novel Antiviral Lipocyclodepsipeptide
    Shimura Satomi; Ishima Masahiro; Ota Ikue; Tsutsui Etsuko; Kamisuki Shinji; Murata Hiroshi; Yamazaki Takayuki; Suzuki Takahiro; Kuramochi Koji; Takeuchi Toshifumi; Kobayashi Susumu; Sugawara Fumio, Symposium on the Chemistry of Natural Products, symposium papers, 55, 0, 2013
    <p> MA026, a novel lipocyclodepsopeptide, was isolated from the fermentation broth of Pseudomonas sp. RtIB026 found in digestive tracts of rainbow trout. This natural product exhibits antiviral activity against infectious hematopoietic necrosis virus (IHNV) and several enveloped viruses. MA026 has a potential to create a novel antiviral drug and more biological characterizations are required. To conduct further studies to reveal the mode of action, a flexible chemical synthesis and modifications are essential. Herein, we provide the first total synthesis of MA026 and phage display screening to identify the target. MA026 consists of cyclodepsipeptide, chain peptide and N-terminal (R)-3-hydroxydecanoic acid. To maximize the convergency, MA026 was divided into two key segments, side chain 2 and cyclodepsipeptide 3. Key to the preparation of 3 was the macrocyclization of decadepsipeptide which relies on the macrocyclization site. Two macrocyclization sites were examined and the macrocyclization at D-Gln<sup>11</sup>-L-Leu<sup>12</sup> furnished cyclodepsipeptide 3 successfully. To reveal the mechanism of antiviral activity, we synthesized biotinylated MA026 and MA026-immobilized PEGA resins. Phage display screenings using these probes were performed to afford peptide sequences that would interact with MA026.</p>, Symposium on the Chemistry of Natural Products Steering Committee, Japanese
  • 縮環系骨格の構築法を基にした天然物の合成
    鈴木 孝洋, 上原記念生命科学財団研究報告集, 27, 1, 6, 2013
    上原記念生命科学財団, Japanese
  • P-25 Synthetic Study of Pyrrocidine B(Poster Presentation)
    Tanaka Ryo; Ohishi Kentaro; Takanashi Noriyuki; Nagano Tomohiko; Suizu Hiroshi; Suzuki Takahiro; Kobayashi Susumu, 天然有機化合物討論会講演要旨集, 54, 339, 344, 01 Sep. 2012
    In 2002, pyrrocidine A and B were isolated from the fermentation broth of a fungus, LL-Cyan 426, as antimicrobial agents against Gram-positive bacteria including drug-resistant strains. Structural features of pyrrocidines are tricyclic decahydrofluorene core (ABC-ring) and 13-membered macrocycle containing para-substituted aryl ether moiety. The complex molecular architecture of these compounds makes them very attractive target molecules for total synthesis. We report herein the stereoselective synthesis of decahydrofluorene 21 which provides the first entry to the ABC-ring moiety of pyrrocidines. The synthesis of 21 commenced with the construction of the C-ring moiety. The cyclic carbon skeleton was synthesized via Diels-Alder reaction between dimethyl-substituted Danishefsky-Yan diene 7 and trisubstituted alkene 8 to afford a diastereomeric mixture of cyclohexenone 10a-b. The ketone 11a possessing the desired configuration was mainly obtained by thermal epimerization of the diastereomeric mixture of 11a-c. Ring-closing metathesis reaction of diene 15, followed by Dess-Martin oxidation afforded the cyclic dienophile 16. Diels-Alder reaction between Danishefsky-Kitahara diene 5 and bicycloenone 16, and the sequential acidic treatment gave diketone 4, establishing the tricyclic carbon framework of 21. Owing to the inherent convex-face selectivity of cis-fused bicyclic AB-ring moiety of 4, nitrile 19 was stereoselectively synthesized in several steps. Vinyl group was introduced to 4 from concave face selectively, avoiding the adjacent cyano group, in two steps to afford ketone 20. The reduction of ketone group from convex face of 20, followed by Chugaev elimination furnished decahydrofluorene 21., Symposium on the chemistry of natural products, Japanese
  • Synthetic studies of MA026, A novel antiviral lipocyclodepsipeptide
    S. Shimura; M. Ishima; Ota, I; E. Tsutsui; S. Kamisuki; H. Murata; T. Yamazaki; T. Suzuki; K. Kuramochi; T. Takeuchi; K. Watashi; S. Kobayashi; F. Sugawara, PLANTA MEDICA, 78, 11, 1283, 1283, Aug. 2012
    English, Summary international conference
  • P-8 Synthetic Study of Atropurpuran(Poster Presentation)
    Suzuki Takahiro; Sasaki Aya; Kobayashi Susumu, 天然有機化合物討論会講演要旨集, 53, 505, 510, 02 Sep. 2011
    In 2009, Wang and colleagues reported the isolation of a structurally unique non-alkaloidal diterpene, atropurpuran, from Aconitum hemsleyanum var. atropurpureum. The structure of atropurpuran features an unprecedented cage-like skeleton consisting of five six-membered rings. Intriguingly, B, C, D, and E ring constitute the tetracyclo[5.3.3.0^<4'9>.0^<4'12>]tridecane skeleton into which two bicyclo[2.2.2]octane are comprised. Despite of these biosynthetically and structurally intriguing properties of tetracyclo[5.3.3.0^<4'9>.0^<4'12>]tridecane skeleton, no synthetic effort has been reported so far. Herein, we report the first entry for the construction of tetracyclic skeleton and the pentacyclic carbon framework of atropurpuran via an intramolecular reverse electron-demand Diels-Alder (REDDA) reaction of masked o-benzoquinone (MOB). The preparation of REDDA precursor was started from o-eugenol 1. Tetralone 4 was successfully converted to ketone 7. Reduction of ketone 7 with DIBAL, silyl etherification, followed by oxidation with Phl(OAc)_2 afforded REDDA precursor 10d. The REDDA reaction of silyl ether 10d (180℃, 1h) afforded tetracyclic 11d in high yield almost as a single diastereomer. Next, we proceeded to the construction of pentacyclic skeleton toward the total synthesis of atropurpuran. Addition of allylmagnesium bromide to ketone 7, ring-closing metathesis gave tricyclic 15. Oxidation of tricyclic 15 with Phl(OAc)_2 and followed by REDDA reaction of resulting MOB was achieved to construct the pentacyclic 14. Finally, hydrogenation of 15 and subsequent dehydration (Tf_2O, pyridine) afforded 16 to complete the construction of the pentacyclic framework of atropurpuran., Symposium on the chemistry of natural products, Japanese
  • P-62 Synthetic Studies of MA026(Poster Presentation)
    Shimura Satomi; Ishima Masahiro; Ota Ikue; Tsutsui Etsuko; Kamisuki Shinji; Murata Hiroshi; Yamazaki Takayuki; Suzuki Takahiro; Kuramochi Koji; Takeuchi Toshifumi; Kobayashi Susumu; Sugawara Fumio, 天然有機化合物討論会講演要旨集, 53, 667, 672, 02 Sep. 2011
    MA026, a novel lipocyclodepsipeptide, exhibits selective antiviral activity against enveloped viruses such as influenza and herpes. An antiviral compound with complex depsipeptide structure like MA026 is scarce, and MA026 has the potential to inhibit viral infections with a novel mechanism. However, the availability of MA026 from natural resources is limited, therefore, the chemical synthesis is essential to accomplish the biological investigation. Here, we present synthetic studies to establish an efficient synthetic pathway to MA026. MA026 consists of (3R)-hydroxydecanoic acid, linear peptide six amino acids and cyclodepsipeptide eight amino acids. Nine of the amino acids posses the D-configuration. The retrosynthetic analysis of MA026 (1) is shown in Figure 2. MA026 was devided into three key segments to maximize the convergency : branched cyclic depsipeptide 2, tripeptide 3 and fatty acid moiety 4. Key to the total synsthesis of MA026 is the macrocyclization of depsipeptide, so we chose two macrocyclization sites, (A) D-Val - D-Leu and (B) L-Leu - D-Gln. Protected amino acids were condensed to gave tripeptide 3. Fatty acid moiety 4 was synthesized from n-octylaldehyde through samarium mediated Reformatsky reaction. The macrocyclization substrate 5 was prepared by the condensation of peptide fragments. Then, 5 was cyclized and the formation of branched cyclic peptide 2 was confirmed by mass spectorometry, however, the 2 was not obtained as a single compound. Five dipeptides were condensed to gave the macrocyclization substrate 6. Attempts to cyclize the precursor 6 is in progress., Symposium on the chemistry of natural products, Japanese
  • 2カルバ環状ホスファチジン酸光学異性体の合成とその生理作用の検討
    野崎 絵美; 後藤 真里; 堀田 晴美; 花澤 修和; 鈴木 孝洋; 小林 進; 室伏 きみ子, 脂質生化学研究, 53, 264, 266, 28 Apr. 2011
    Japanese
  • 抗腫瘍活性天然ポリケチド(+)-TMC-151Cの収束的全合成
    松井亮介; 瀬戸健太郎; 佐藤優奈; 藤田和弘; 鈴木孝洋; 中崎敦夫; 小林進, 日本化学会講演予稿集, 91st, 4, 2011
  • 28-Deacetylbelamcandalの合成研究
    高梨憲幸; 田村圭司; 邊見和輝; 鈴木孝洋; 中崎敦夫; 小林進, 反応と合成の進歩シンポジウム講演要旨集, 37th, 2011
  • Design and synthesis of molecular probe for identifying intracellular protein target
    Aya Toizaki; Aiko Suzuki; Atsuo Nakazaki; Takahiro Suzuki; Yoichi Takakusagi; Fumio Sugawara; Kengo Sakaguchi; Susumu Kobayashi, International Symposium on Technologies against Cancer (ISTC2011), 2011
    English, Summary national conference
  • Synthetic Study on 28-Deacetylbelamcandal
    Takanashi Noriyuki; Tamura Keiji; Henmi Kazuki; Suzuki Takahiro; Nakazaki Atsuo; Kobayashi Susumu, Proceedings of the Symposium on Progress in Organic Reactions and Syntheses, 37, 0, 77, 77, 2011
    A spiroiridal triterpenoid, 28-Deacetylbelamcandal was isolated from the rhizomes of <I>Belamcanda chinensis</I> in 1991. This natural product possesses a spiro[4.5]decane framework including five contiguous stereogenic centers and a tetrasubstituted olefin.<BR>Our strategy towards 28-Deacetylbelamcandal features Claisenrearrangement in alkenyl dihydropyran system for construction of a highly functionalized spiro[4.5]decane framework and stereoselective synthesis of tetrasubstituted olefin via intramolecular Heck reaction, subsequent deprotonation at bisallylic position and Rubottom oxidation.<BR>Alkenyl dihydropyran was prepared in 8 steps involving asymmetric aldol reaction and acid-catalyzed cyclization. The Claisen rearrangement (in triglyme, 0.05 M, 230 <SUP>o</SUP>C, 4 hr.) gave the desired product in 84% yield. Conversion of the Claisen product to the precursor for Heck reaction is currently under way., Division of Organic Chemistry, The Pharmaceutical Society of Japan, Japanese
  • Synthetic Study of Chloropupukeananin
    Suzuki Takahiro; Miyajima Yuria; Suzuki Kaname; Koshimizu Masaki; Kobayashi Susumu, Proceedings of the Symposium on Progress in Organic Reactions and Syntheses, 37, 0, 51, 51, 2011
    Chloropupukeananin (<B>1</B>) was isolated from <I>Pestalotiopsis fici</I> by Che and colleagues as a new inhibitor against HIV-1 replication. The array of functional groups in a rigid tricyclic structure of <B>1</B> has provided us with a strong motive to construct the pupukeanane core based on biosynthetic hypothesis. We proposed a biosynthetic pathway for chloropupukeananin via maldoxin involving a reverse electron-demand Diels-Alder (REDDA) reaction and an intramolecular carbonyl-ene reaction. Herein, we report the investigation of REDDA and carbonyl-ene reaction with a model of maldoxin and vinylallene.<BR>The precursors of REDDA were subjected to high pressure conditions to give a major product and other isomers. The X-ray crystallographic analysis of the major product revealed that the precursors underwent the REDDA reaction and the intramolecular carbonyl-ene reaction to construct the pupukeanane core in a single operation., Division of Organic Chemistry, The Pharmaceutical Society of Japan, Japanese
  • Total Synthesis of (+)-TMC-151C Using Vinylogous Mukaiyama Aldol Reaction and Ring Closing Metathesis
    Matsui Ryosuke; Seto Kentaro; Sato Yuna; Fujita Kazuhiro; Suzuki Takahiro; Nakazaki Atsuo; Kobayashi Susumu, 天然有機化合物討論会講演要旨集, 52, 13, 18, 01 Sep. 2010
    We have previously developed a highly stereoselective vinylogous Mukaiyama aldol reaction (VMAR) usin gvinylketene silyl N,O-acetal 1, which provides a unique and remarkable entry to a remote asymmetric induction. From a synthetic point of view, this method can directly afford th anti-δ-hydroxy-α,γ-dimethol-α,β-unsaturated carbonyl unit, which is seen in many naturally occurring products. In fact, VMAR has successfully been utilized in the total syntheses of various biologically active compounds by many groups including us. Se envisioned that the VMAR would be an efficient and powerful methodology for the synthesis of (+)-TMC-151C (2). This compound was isolated from Gliocladium sp. by the research group of Tanabe Seiyaku in 1999, and it shows the cytotoxicity to wide-rangingg tumor cell lines, such as HCT-116, B16 and HeLa. The structural significance as well as the biological property has stimulated the synthesis of TMC-151C (2). Herein, we report the first total synthesis of (+)-TMC-151C (2) using VMAR and Ring-Closing Metathesis (RCM) via a highly convergent synthetic route. Characteristic features of the present synthesis include: 1) the construction of C_1-C_5 segmetn and C_9-C_<13> segment was successfully achieved by VMAR, and 2) the stereoselective formation of C_6-C_7 double bond was accomplished by developing a unique E-olefin forming 8-membered RCM of silicon-tethered diene. Moreover, we observed a unique E-olefin forming 8-memberes ring RCM of silylene acetals, and proposed a plausible transition state as well as the structural requirement for E-olefin forming RCM. Although the E-olefin was produced only in a limited case, this methodology was quite useful for the total synthesis of TMC-151C (2)., Symposium on the chemistry of natural products, Japanese
  • 自然が産み出す複雑さへの挑戦 : ビニグロールの全合成(A 化学系薬学)
    鈴木 孝洋, ファルマシア, 46, 7, 686, 687, 01 Jul. 2010
    公益社団法人日本薬学会, Japanese
  • Zoanthamineの合成研究
    皆迫洋平; 山下大輔; 中崎敦夫; 鈴木孝洋; 小林進, 日本薬学会年会要旨集, 130th, 2, 2010
  • 抗腫瘍性環状リン脂質の硫黄誘導体(thia-cPA)の合成および生物活性評価
    田中遼; 加藤賢; 後藤真里; 野崎絵美; 花澤修和; 中崎敦夫; 鈴木孝洋; 室伏きみ子; 小林進, 日本薬学会年会要旨集, 130th, 2, 2010
  • ゾアンタミンアルカロイドの合成研究
    山下大輔; 皆迫洋平; 中島雄大; 中崎敦夫; 鈴木孝洋; 小林進, 次世代を担う有機化学シンポジウム講演要旨集, 8th, 2010
  • ノルゾアンタミンのCDEFG環の構築 4位メチル基の環化への影響
    中島雄大; 山下大輔; 鈴木要; 中崎敦夫; 鈴木孝洋; 日景尚睦; 小林進, 複素環化学討論会講演要旨集, 40th, 2010
  • PI-PLC特異的阻害物質(+)-Akaterpinの合成と構造決定
    細井勇人; 河井伸之; 萩原秀樹; 鈴木孝洋; 中崎敦夫; 小林進, 有機合成シンポジウム講演要旨集, 98th, 2010
  • Claisen転位を基盤としたHistrionicotoxin類の合成研究
    齊藤洋平; 中崎敦夫; 鈴木孝洋; 小林進, 日本薬学会年会要旨集, 130th, 2, 2010
  • AngiomotinとAngiostatin及びRoxithromycinとの結合領域及び結合様式の解明
    高草木香織; 鈴木愛こ; 高草木洋一; 渡辺まどか; 松本勇記; 戸井崎絢; 鈴木孝洋; 中崎敦夫; 菅原二三男; 坂口謙吾, 生化学, 2010
  • Exploration of Small-molecule-binding Proteins Using QCM-PD Method
    Toizaki Aya; Suzuki Aiko; Nakazaki Atsuo; Suzuki Takahiro; Takakusagi Yoichi; Sugawara Fumio; Sakaguchi Kengo; Kobayashi Susumu, Proceedings of the Symposium on Progress in Organic Reactions and Syntheses, 36, 0, 44, 44, 2010
    We attempted an identification of the molecular target of an antibiotic roxithromycin (RXM) using a T7 phage display (PD) screen on a quartz-crystal microbalance (QCM) device (QCM-PD). Wherein, we synthesized a RXM derivative that forms a self-assembled monolayer (SAM) for a specific RXM immobilization on the gold electrode surface of a QCM sensor chip. We then performed a one-cycle selection of RXM-binding peptides from a library of T7 phage-displayed peptides. As a result, we obtained 25 of RXM-recognizing sequences. Subsequent analysis utilizing the subset of sequence and receptor ligand contacts (RELIC) software clearly pinpointed several amino-acid residues within the RXM-binding site on the well-known direct targets, CYP3A4. Our findings demonstrate the effectiveness of this methodology and general applicability for a wide range of small-molecules. We are currently searching for another target responsible for anti-angiogenic effect of RXM., Division of Organic Chemistry, The Pharmaceutical Society of Japan, Japanese
  • Synthetic Study of atropurpuran
    Sasaki Aya; Suzuki Takahiro; Kobayashi Susumu, Proceedings of the Symposium on Progress in Organic Reactions and Syntheses, 36, 0, 38, 38, 2010
    Atropurpuran was isolated from the roots of <I>Aconitum hemsleyanum var. atropurpureum</I> in 2009. Structurally, atropurpuran possesses an unprecedented skeleton, bis-bicyclo[2.2.2]octane, that includes a quaternary carbon shared with six six-membered rings.<BR>At the outset of our synthetic investigation on atropurpuran, we initially attempted to establish an efficient methodology for constructing a tetracyclic cage sketlon by employing an intramolecular reverse electron-demand Diels-Alder (REDDA) reaction. The preparation of REDDA precursor, having both MOB moiety and dienophile side chain, was achieved in 11 steps from guaiacol.<BR>The REDDA reaction of triene (in mesitylene, 180<SUP>o</SUP>C, 1 h) produced the desired cycloadduct in 77% yield. The structure of the cycloadduct was confirmed by NMR spectroscopy., Division of Organic Chemistry, The Pharmaceutical Society of Japan, Japanese
  • T7ファージディスプレイ法を用いて同定したアンジオモチンとロキシスロマイシンの相互作用の検証
    鈴木愛こ; 高草木洋一; 渡辺まどか; 松本勇記; 戸井崎絢; 鈴木孝洋; 菅原二三男; 小林進; 坂口謙吾, 日本分子生物学会年会講演要旨集, 32nd, Vol.4, 2009
  • Pseudodeflectusinの合成研究
    佐藤優奈; 野中美穂; 鈴木孝洋; 中崎敦夫; 小林進, 日本薬学会関東支部大会講演要旨集, 53rd, 2009
  • TMC-151Cの全合成を目指したE選択的8員環形成閉環メタセシス反応の開発
    松井亮介; 瀬戸健太郎; 藤田和弘; 中崎敦夫; 鈴木孝洋; 小林進, 有機合成シンポジウム講演要旨集, 96th, 2009
  • Synthesis and structure determination of PI-PLC specific inhibitor Akaterpin
    Hosoi Hayato; Kawai Nobuyuki; Hagiwara Hideki; Suzuki Takahiro; Nakazaki Atsuo; Kobayashi Susumu, Proceedings of the Symposium on Progress in Organic Reactions and Syntheses, 35, 0, 15, 15, 2009
    Akaterpin, a specific inhibitor of PI-specific PLC, consists of two decalin rings and a hydroquinone disulfate moiety. Relative stereochemistry of each decalin moiety was determined dependently, and, therefore, relative structure has not been yet determined. Our strategy to akaterpin was to construct the upper decalin first, and construct the lower dacalin by intramolecular Diels-Alder reaction. The resulting two isomers were separated, and each isomer was transformed to the target molecule. We found that the H-NMR spectrum of the target molecule (racemic) derived from the major isomer of Diels-Alder reaction was found to be identical to that of natural akaterpin. Thus, we were able to achieve a total synthesis of akaterpin (racemic) and determine the relative stereochemistry., Division of Organic Chemistry, The Pharmaceutical Society of Japan, Japanese
  • 36 Asymmetric Total Synthesis of Antitumor Compound, (-)-FR182877(Oral Presentation)
    Tanaka Natsumi; Suzuki Takahiro; Matsumura Takehiko; Hosoya Yosuke; Nakada Masahisa, 天然有機化合物討論会講演要旨集, 50, 239, 244, 01 Sep. 2008
    (-)-FR182877 was isolated from the fermentation broth of Streptomyces sp. No. 9885 by a research group of Fujisawa Pharmaceutical Company in 1998. This compound possesses an unprecedented hexacyclic ring system containing a bridgehead double bond as part of a vinylogous carbonate unit and 12 stereogenic centers, and exhibits microtubule stabilizing activity similar to that of Taxol. Hence, the complex structure and promising bioactivity of (-)-FR182877 have attracted considerable attention from synthetic chemists. Our synthetic approach began with the conversion of known aldehyde 8 to precu..., 天然有機化合物討論会, Japanese
  • P-453 STUDIES ON ASYMMETRIC TOTAL SYNTHESIS OF (-)-FR182877
    Tanaka Natsumi; Suzuki Takahiro; Hosoya Yosuke; Nakada Masahisa, International Symposium on the Chemistry of Natural Products, 2006, "P, 453", 23 Jul. 2006
    Symposium on the chemistry of natural products, English
  • Synthetic studies on FR182877
    T Suzuki; T Matsumura; N Tanaka; M Nakada, ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 229, U514, U514, Mar. 2005
    English, Summary international conference
  • First total synthesis of antimitotic compound, (+)-phomopsidin
    T Suzuki; K Usui; Y Miyake; M Namikoshi; M Nakada, ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 229, U513, U513, Mar. 2005
    English, Summary international conference
  • 92(P-20) Synthetic Studies on Phomopsidin
    Suzuki Takahiro; Miyake Yoshiharu; Usui Kenji; Nakada Masahisa; Namikoshi Michio, 天然有機化合物討論会講演要旨集, 45, 545, 550, 01 Sep. 2003
    Phomopsidin was isolated from Phompsis sp. TUF95F47 by Namikoshi and co-workers in 1997, and its absolute structure and biological activity have been reported. Phomopsidin and its geometrical isomer (MK8383) showed potent inhibitory activity against assembly of microtubule proteins, exhibiting strong antitumor activity. It has been proposed that phomopsidin could be generated via the IMDA reaction of 1. Therefore, the potent antitumor activity and this biosynthetic background draw our attention to the synthesis of phomopsidin. We planned to synthesize the cis-decalin core 2 of phomopsidin f..., 天然有機化合物討論会, Japanese
  • Asymmetric Catalysis of Nozaki–Hiyama Allylation and Methallylaton with A New Tridentate Chiral Ligand
    Inoue Masahiro; Suzuki Takahiro; Nakada Masahisa, Proceedings of the Symposium on Progress in Organic Reactions and Syntheses, 29, 0, 210, 211, 2003
    We describe the development of a new tridentate chiral ligand effective for the asymmetric catalysis of Nozaki&mdash;Hiyama allylation, methallylation and propargylation. Various aldehydes (aromatic and aliphatic) were generally allylated or methallylated with good to excellent enantioselectivity (86-96% ee). The enantioselective reaction catalyzed by this Cr-ligand complex has great potential for natural product synthesis, and a key intermediate of calcitriol lactone synthesis was obtained with excellent diastereoselectivity (97% de, 91%). Another remarkable feature of this ligand is the stability of the Cr-ligand complex which was recovered after the enantioselective reaction and recycled without diminishing the enantioselectivity and yield., Division of Organic Chemistry, The Pharmaceutical Society of Japan
■ Books and other publications
  • 有機合成実験法ハンドブック第2版
    小林進; 鈴木孝洋, 16章 アルドール反応
    丸善出版, Nov. 2015, [Joint work]
  • 有機合成実験法ハンドブック 第2版
    鈴木孝洋, 15 官能基の保護と脱保護
    丸善出版, Nov. 2015, 9784621089484, 1166, 315-357, Japanese, Scholarly book, [Joint editor]
■ Lectures, oral presentations, etc.
  • Synthetic Studies of Complex Natural Products by One-step Framework Construction Strategies
    Takahiro Suzuki
    11th Singapore International Chemistry Conference, English, Invited oral presentation
    11 Dec. 2022 - 14 Dec. 2022, 33431038;10810282, [Invited]
  • Biomimetic Total Syntheses of Chloropestolides, and Chloropupukeananin
    Takahiro Suzuki
    International Congress on Pure & Applied Chemistry (ICPAC) Kota Kinabalu 2022, English, Invited oral presentation
    22 Nov. 2022 - 27 Nov. 2022, 33431038;10810282, [Invited]
  • Total Synthesis of Complex Natural Products Based on Diels-Alder Reaction
    Takahiro Suzuki
    Keio International;Symposium on;Innovative;Synthesis of Complex Molecules, 14 Dec. 2019, English, Invited oral presentation
    33431038;10810282, [Invited]
  • Total Syntheses of Complex Natural Products by Rapid Framework Construction Strategies
    Takahiro Suzuki
    Hokkaido mini-Symposium by Young Generations in Asia, 15 Nov. 2019, English, Invited oral presentation
    33431038;10810282, [Invited]
  • Biomimetic Total Synthesis of Chloropupukeananin
    Takahiro Suzuki
    The 14th International Conference on Cutting-Edge Organic Chemistry in Asia, 28 Sep. 2019, English, Poster presentation
    33431038;10810282, [Invited]
  • 新規香料化合物の創製に向けたジバレラン骨格の改良合成法の開発
    岡本ゆきの; 和田善行; 村西修一; 鈴木孝洋; 谷野圭持
    The 62nd Symposium on the Chemistry of Terpenes, Essential Oils and Aromatics, 14 Oct. 2018, Japanese, Oral presentation
    [Domestic Conference]
  • Total Synthesis of Atropurpuran
    Takahiro Suzuki; Kenta Nakanishi; Takeshi Koyama; Susumu Kobayashi; Keiji Tanino
    22nd International Conference on Organic Synthesis (22-ICOS), 17 Sep. 2018, English, Oral presentation
    [International presentation]
  • アトロプルプランの不斉全合成研究
    古山岳史; 鈴木孝洋; 谷野圭持
    第53回天然物化学談話会, 05 Jul. 2018, Japanese, Poster presentation
    [Domestic Conference]
  • ヘチダン型ジテルペンの 収束的骨格構築法の開発
    池田航; 鈴木孝洋; 谷野圭持
    第53回天然物化学談話会, 04 Jul. 2018, Japanese, Poster presentation
    [Domestic Conference]
  • ent-カウレンジテルペノイドKamebaninの全合成研究
    菅野彩夏; 鈴木孝洋; 谷野圭持
    日本化学会第98春季年会, 23 Mar. 2018, Japanese, Oral presentation
    [Domestic Conference]
  • 3-ヒドロキシ-2-ピロンを用いた新規[4+3]付加環化反応の開発
    柳澤尚宗; 鈴木孝洋; 谷野圭持
    日本化学会第98春季年会, 22 Mar. 2018, Japanese, Oral presentation
    [Domestic Conference]
  • 特異な構造の天然物の全合成と拡散的研究展開
    Takahiro Suzuki
    化学系学協会北海道支部2018年冬季研究発表会, 17 Jan. 2018, Japanese, Invited oral presentation
    [Invited], [Domestic Conference]
  • Total Synthesis of Atropurpuran
    Takahiro Suzuki
    59th Symposium on the Chemistry of Natural Products, 20 Sep. 2017, Japanese, Oral presentation
    [Domestic Conference]
  • 付加環化反応を基盤とした特異な環構造を有するテルペノイドの全合成研究
    Takahiro Suzuki
    The 61nd Symposium on the Chemistry of Terpenes, Essential Oils and Aromatics, 09 Sep. 2017, Japanese, Invited oral presentation
    [Invited], [Domestic Conference]
  • Enantioselective Total Synthesis of (+)-iso-A82775C
    Takahiro Suzuki
    International Symposium on Pure & Applied Chemistry (ISPAC) 2017, 10 Jun. 2017, English, Invited oral presentation
    [Invited], [International presentation]
  • アトロプルプランの全合成
    中西健太; 鈴木孝洋; 小林進; 谷野圭持
    日本化学会第97春季年会, 18 Mar. 2017, Japanese, Oral presentation
    [Domestic Conference]
  • iso-A82775Cの不斉全合成
    渡邉壮一郎; 鈴木孝洋; 谷野圭持
    日本化学会第97春季年会, 18 Mar. 2017, Japanese, Oral presentation
    [Domestic Conference]
  • アイボレノイドAの全合成研究
    堀口耕作; 鈴木孝洋; 谷野圭持
    The 60th Symposium on the Chemistry of Terpenes, Essential Oils and Aromatics, 30 Oct. 2016, Japanese, Oral presentation
    [Domestic Conference]
  • 連続的環化反応を利用したent-カウレン類の合成研究
    菅野彩夏; 鈴木孝洋; 谷野圭持
    The 60th Symposium on the Chemistry of Terpenes, Essential Oils and Aromatics, 30 Oct. 2016, Japanese, Oral presentation
    [Domestic Conference]
  • Studies toward the Biomimetic Total Synthesis of Chloropupukeananin
    Takahiro Suzuki; Susumu Kobayashi; Keiji Tanino
    11th International Conference on Cutting-Edge Organic Chemistry in Asia, 29 Oct. 2016, English, Poster presentation
    [Invited], [International presentation]
  • iso-A82775Cの全合成研究
    渡邉壮一郎; 鈴木孝洋; 谷野圭持
    日本化学会北海道支部2016年夏季研究発表会, 23 Jul. 2016, Japanese, Oral presentation
    [Domestic Conference]
  • iso-A82775Cの全合成研究
    渡邉壮一郎; 鈴木孝洋; 谷野圭持
    第51回天然物化学談話会, 07 Jul. 2016, Japanese, Poster presentation
    [Domestic Conference]
  • Synthesis and properties of novel Odorants containing Dibarrelane skeleton
    和田善行; 鈴木孝洋; 吉田啓; 鈴木真也; 中西健太; 佐久間克也; 作田圭亮; 谷野圭持; 清水功雄
    Annual Meeting 2016 Sapporo of Japan Society for Bioscience, Biotechnology, and Agrochemistry, 28 Mar. 2016, Japanese, Poster presentation
    [Domestic Conference]
  • Construction of Cage-like Tricyclic Skeleton of Chloropupukeananin, an Inhibitor of HIV-1 Replication
    Takahiro Suzuki; Susumu Kobayashi; Keiji Tanino
    4th International Postgraduate Conference on Pharmaceutical Science, 27 Feb. 2016, English, Invited oral presentation
    [Invited], [International presentation]
■ Syllabus
  • 生物化学Ａ（Ⅳ）, 2024年, 修士課程, 総合化学院
  • 有機合成化学, 2024年, 学士課程, 理学部
■ Research Themes
  • かご状飽和炭化水素合成のリビジット～一段階多環構築戦略による超効率的合成
    科学研究費助成事業
    01 Apr. 2024 - 31 Mar. 2028
    鈴木 孝洋
    日本学術振興会, 基盤研究(B), 北海道大学, 24K01476
  • Innovative approach to illisimonin A by one-step multi-ring construction strategy
    Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)
    01 Apr. 2020 - 31 Mar. 2023
    鈴木 孝洋
    立体的に複雑な縮環構造（高次構造）を有する天然有機化合物（天然物）は、有用な生物活性を示すものが多く、医薬品・農薬として利用されてきた。それらの多くは有機化学的に合成されているが、依然として合成未達成のものも残されている。申請者の提案する「一段階多重環構築戦略」は、これらの合成困難な高次構造天然物に対する有効なアプローチであると考えている。そこで本研究では、近年シキミ属植物から単離が報告されたイリシモニンAを標的化合物とし、全合成を達成することで「一段階多重環構築戦略」の有用性を実証することにした。
    昨年度に引き続き、イリシモニンAの骨格合成に向けてモデル化合物を用いた検討を行った。アロセドラン骨格からイリシモニンA骨格への骨格転位反応は、当初ベンジル酸転位による反応機構で進行すると推定していたが、詳細な反応条件の検討の結果、レトロクライゼン反応/アルドール反応の二段階の反応によって起きていることを明らかにした。これにより全合成達成には、ビシクロ[2.2.2]オクタン上の3つのケト基が必須であることが判明した。しかしながら、レトロクライゼン反応/アルドール反応によって生じるα-ヒドロキカルボン酸は望みでない立体化学の異性体が優先して得られているため、選択性の改善が今後の課題である。
    現在イリシモニンAの全合成に向けて、すべての必要な官能基を備えた基質をもちいた合成に着手し、アロセドラン骨格の合成段階を検討している。
    Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (C), Hokkaido University, 20K05485
  • Development and Application of Highly Stereoselective Aldol Reactions Using Chiral Amide
    Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B)
    2010 - 2012
    KOBAYASHI Susumu; SUZUKI Takahiro
    Diastereoselective reactions using chiral amide have extensively been utilized in the chiral synthesis of complex molecules in these decades.In this context, we have developed two types of diastereoselective aldol reactions. In the present investigation, we focused on (1) further improvement of vinylogous Mukaiyama aldol reaction, (2) general applicability of the stereocontrol of 1,2-diol including tertiary alcohol, and (3) application to biologically significant naturally occurring compounds.
    Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Tokyo University of Science, 22390004