9-表塞西利福酰胺 J 的简洁非对映全合成

Concise asymmetric total synthesis of 9-epi-sessilifoliamide J.

机构信息

Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, PR China.

出版信息

Org Lett. 2011 Oct 7;13(19):5270-3. doi: 10.1021/ol202140y. Epub 2011 Aug 31.

DOI:10.1021/ol202140y

PMID:21879702

Abstract

A 10-step asymmetric synthesis of 9-epi-sessilifoliamide J (20), together with sessilifoliamide J (6), has been accomplished from the key chiral building block 11 via a threo-selective vinylogous Mannich reaction and a Ley oxidation-SmI(2)-mediated coupling lactonization. The absolute configuration of the natural sessilifoliamide J was established.

摘要

从关键手性砌块 11 出发，通过 threo-选择性的 vinylogous Mannich 反应和 Ley 氧化-SmI(2)-介导的偶联内酯化反应，完成了 9-epi-sessilifoliamide J（20）和 sessilifoliamide J（6）的 10 步不对称全合成。确定了天然 sessilifoliamide J 的绝对构型。