Enantioselective Total Synthesis of (鈭?-Walsucochin B

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• 作者：Shiyan Xu ; Jixiang Gu ; Huilin Li ; Donghui Ma ; Xingang Xie ; Xuegong She
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：April 4, 2014
• 年：2014
• 卷：16
• 期：7
• 页码：1996-1999
• 全文大小：312K
• 年卷期：v.16,no.7(April 4, 2014)
• ISSN：1523-7052

文摘

The first enantioselective total synthesis of the structurally unique nortriterpenoid (鈭?-walsucochin B has been accomplished through the cationic polyolefin cyclization initiated by chiral epoxide. The core framework and the stereocenters in the natural product were all constructed in this step. A site-selective, late-stage free-radical halogenation and Seyferth鈥揋ilbert homologation was adopted to install the acetylene moiety to synthesize the phenylacetylene. The absolute configuration of walsucochin B was confirmed through enantioselective total synthesis.