Enantioselective synthesis of 5-substituted α,β-unsaturated δ-lactones:: application to the synthesis of styryllactones

被引：39

作者：

Harris, JM ^{[1
]}

O'Doherty, GA ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 02期

关键词：

sharpless dihydroxylation; asymmetric synthesis; lactones; carbohydrates;

D O I：

10.1016/S0040-4039(99)02050-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A flexible enantioselective synthesis of highly functionalized 5-substituted alpha,beta-unsaturated delta-lactones has been achieved by applying the Sharpless catalytic asymmetric dihydroxylation to vinylfuran as the key step. The resulting diols are produced in high enantio excess and can be stereoselectively transformed into differentially protected delta-lactones through a short reaction sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：183 / 187

页数：5

共 33 条

[1]

ARGOUDEL.AD, 1966, TETRAHEDRON LETT, P1969

[2] Julia-Colonna asymmetric epoxidation of furyl styryl ketone as a route to intermediates to naturally-occurring styryl lactones [J].