Synthesis of (+)-Didemniserinolipid B via Ketalization/Ring-Closing Metathesis

详细信息    查看全文

• 作者：Christopher C. Marvin ; Eric A. Voight ; Steven D. Burke
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：December 20, 2007
• 年：2007
• 卷：9
• 期：26
• 页码：5357 - 5359
• 全文大小：80K
• 年卷期：v.9,no.26(December 20, 2007)
• ISSN：1523-7052

文摘

ABLE>A modular synthesis of didemniserinolipid B is reported. Central to this synthesis was the use of a ketalization/ring-closing metathesis (K/RCM) strategy to establish the 6,8-dioxabicyclo[3.2.1]octane core. The C10 axial alcohol was established via a selective epoxidation, followedby reductive trans-diaxial epoxide opening. The serinol and unsaturated ester side chains were introduced by a Williamson etherification andcross metathesis, respectively.