Total Synthesis of the 7,10‐Epimer of the Proposed Structure of Amphidinolide N,Part II: Synthesis of C17–C29 Subunit and Completion of the Synthesis |
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| Authors: | Dr. Koji Ochiai Dr. Sankar Kuppusamy Yusuke Yasui Kenji Harada Dr. Nishant R. Gupta Dr. Yohei Takahashi Prof. Dr. Takaaki Kubota Prof. Dr. Jun'ichi Kobayashi Prof. Dr. Yujiro Hayashi |
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| Affiliation: | 1. Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, Japan;2. Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan;3. Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo, Japan;4. +81)?22‐795‐6566;5. Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai, Japan |
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| Abstract: | The total synthesis of 7,10‐epimer of the proposed structure of amphidinolide N was accomplished. The requisite chiral C17–C29 subunit was assembled stereoselectively via Keck allylation, Shi epoxidation, diastereoselective 1,3‐reduction, and a later oxidative synthesis of the THF framework. The C1–C13 and C17–C29 subunits were successfully coupled using a Enders RAMP “linchpin” as the C14–C16 three carbon unit, thereby controlling the chirality at C14 and C16. The labile allyl epoxy moiety was successfully constructed by Grieco–Nishizawa olefination at a final stage of the synthesis. |
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| Keywords: | Enders RMAP Grieco-Nishizawa olefination Keck allylation Shi-epoxidation total synthesis |
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