An Evans-Tishchenko-ring-closing metathesis approach to medium-ring lactones
An Evans-Tishchenko-ring-closing metathesis approach to medium-ring lactones
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DOI：
10.1021/ol062932z
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发表时间：
2007-02-15
期刊：
影响因子：
5.2
通讯作者：
White, John W.
中科院分区：
文献类型：
--
作者：
Aird, Jennifer I.;Hulme, Alison N.;White, John W.
报道了一种基于Evans-Tishchenko和闭环复分解（RCM）反应合成中环内酯的新方法。在不饱和醛与不饱和β-羟基酮的Evans-Tishchenko反应中证明了高的非对映选择性（> 95：5），并且优化了所得二烯的RCM环化条件以得到高产率的中环内酯。该序列的合成效用通过生成完全官能化的octalactin A核心来证明。
A new approach to the synthesis of medium-ring lactones is reported based on sequential Evans-Tishchenko and ring-closing metathesis (RCM) reactions. High diastereoselectivity (> 95:5) is demonstrated in the Evans-Tishchenko reaction of unsaturated aldehydes with unsaturated beta-hydroxy ketones, and conditions for the RCM cyclization of the resultant dienes have been optimized to give high yields of medium ring lactones. The synthetic utility of this sequence is demonstrated through generation of the fully functionalized core of octalactin A.