顺式西维菌素的全合成。

Total synthesis of cis-sylvaticin.

作者信息

Brown Lynda J, Spurr Ian B, Kemp Stephen C, Camp Nicholas P, Gibson Karl R, Brown Richard C D

机构信息

School of Chemistry, University of Southampton, Highfield, Southampton, UK.

出版信息

Org Lett. 2008 Jun 19;10(12):2489-92. doi: 10.1021/ol800767e. Epub 2008 May 20.

DOI:10.1021/ol800767e

PMID:18489103

Abstract

An asymmetric total synthesis of (+)-cis-sylvaticin is described. Key steps include the use of permanganate-mediated oxidative cyclization of 1,5-dienes to synthesize the two major fragments 2 and 3 and a catalytically efficient tethered RCM to unite these THF-containing fragments. In addition, t-BuP 4 base was found to reliably promote rapid alkylation of the butenolide precursor fragment 4.

摘要

描述了(+)-顺式-西维他汀的不对称全合成。关键步骤包括使用高锰酸盐介导的1,5-二烯氧化环化反应来合成两个主要片段2和3，以及使用催化效率高的连接RCM反应将这些含四氢呋喃的片段连接起来。此外，发现叔丁基膦碱能可靠地促进丁烯内酯前体片段4的快速烷基化反应。