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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
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
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
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.
Keywords:Enders RMAP  Grieco-Nishizawa olefination  Keck allylation  Shi-epoxidation  total synthesis
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