An Ireland-Claisen approach to lignans:: Synthesis of the putative structure of 5-epi-eupomatilone-6

被引：24

作者：

Hutchison, JM ^{[1
]}

Hong, SP ^{[1
]}

McIntosh, MC ^{[1
]}

机构：

[1] Univ Arkansas, Dept Chem & Biochem, Fayetteville, AR 72701 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 12期

关键词：

D O I：

10.1021/jo049817r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel Ireland-Claisen approach to the putative structure of eupomatilone-6 is described. The rearrangement established the C3 and C4 stereocenters and concomitantly generated a vinyl epoxide. The C5 oxygen was installed by cyclization of the pentenoic acid carboxyl group onto the vinyl epoxide in an S(N)2' fashion to afford the C5-epi stereochemistry. The natural C5 stereochemistry was accessed via a substrate directed dihydroxylation.

引用

页码：4185 / 4191

页数：7

共 42 条

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