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祷 雄太 (イノリ ユウタ)
| 薬学研究院 創薬科学部門 創薬化学分野 | 助教 |
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■ 論文- Total Synthesis and Complete Stereochemical Assignment of Amphirionin‐5, a Potent Natural Osteoblasts Proliferator
Yusuke Ogura; Kenji Nemoto; Tadafumi Fujita; Yuta Inori; Daisuke Abe; Hironori Okamura; Hirosato Takikawa; Shigefumi Kuwahara
ChemistryEurope, 4, 2, Wiley, 2025年10月26日, ［査読有り］
研究論文（学術雑誌）, Amphirionin‐5, derived from dinoflagellates of the genus Amphidinium , exhibits a unique biological activity whereby trace amounts can lead to potent proliferation of osteoblasts, making it a promising candidate for regenerative therapy of bone and treatment of osteoporosis. However, the relative configuration of amphirionin‐5 has only been partially determined. Herein, the total synthesis of amphirionin‐5 is undertaken to establish its overall stereochemistry. Synthesized C16‐C28 model with the proposed relative configuration of C19‐C23 shows significant discrepancies between its NMR spectroscopic data around C19 and those of the corresponding substructures of the natural amphirionin‐5, suggesting of necessity for reconsideration of the relative configuration of C19. Two further 19 S ‐type C11‐C28 models are synthesized, and detailed NMR analysis reveals that the 13 C NMR of (19 S ,26 R )‐C11‐C28 models show the best agreement with those in the corresponding substructure of the natural product; thus, the relative configurations from C19 to C26 of amphirionin‐5 are proposed as 19 S *, 20 S *, 23 S *, and 26 R *. Coupling of the C1‐C16 segment, synthesized from an optically active α ‐silyloxy pentanolide as a common intermediate, and the (19 S ,26 R )‐C17‐C28 segment is achieved under intermolecular Stetter reaction conditions, enabling the convergent total synthesis of the candidate diastereomer of amphirionin‐5. Ultimately, the overall stereochemistry of amphirionin‐5 is fully assigned. - Asymmetric Total Synthesis of (+)-Karanone: An Important Aroma Compound in Fine Agarwood
Yuta Inori; Hirosato Takikawa; Yusuke Ogura
Journal of Natural Products, 88, 9, 2216, 2224, American Chemical Society (ACS), 2025年08月26日, ［査読有り］, ［筆頭著者］
英語, 研究論文（学術雑誌） - New synthesis of (±)-karanone, an important aroma compound in agarwood
Yuta Inori; Hirosato Takikawa; Yusuke Ogura
Bioscience, Biotechnology, and Biochemistry, 87, 4, 371, 377, Oxford University Press (OUP), 2023年01月25日, ［査読有り］, ［筆頭著者］
英語, 研究論文（学術雑誌）, ABSTRACT
A concise synthesis of (±)-karanone, an important aroma compound of agarwood, was achieved from a commercially available 3-methylcyclohex-2-enol in 3.5% yield in 11 steps. The two contiguous stereocenters at C4 and C5 were constructed via Ireland–Claisen rearrangement. The allylic oxidation at C8 was successfully performed with the mixture of tert-butyl hydroperoxide (TBHP) and CuI. A precursor of ring-closing metathesis to construct a bicyclic dienone was efficiently synthesized from iodoenone by 1,4-addition and nucleophilic substitution of the vinyl group in one pot.
