TOTAL SYNTHESIS OF THE MACROLIDE (+)-ASPICILIN BY AN ASYMMETRICALLY CATALYZED MACROCYCLIZATION OF AN OMEGA-ALKYNAL ESTER

被引：61

作者：

OPPOLZER, W

RADINOV, RN

DEBRABANDER, J

机构：

[1] Département de Chimie Organique, Université de Genève

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 15期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/0040-4039(95)00351-C

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

omega-Alkynal ester 3, prepared from (S)-propylene oxide 4, yields the macrocyclic (6R)-allylic alcohol 2 (60% yield, 83% d.e.) in one operation via monohydroboration, boron/zinc-transmetalation and (-)-DAIB ''catalyzed'' intramolecular alkenylzinc/aldehyde addition. Introduction of the C(2)-C(3) double bond by selenoxide elimination (2 --> 8), hydroxy-directed epoxidation (8 --> 9), acetate assisted alpha-epoxide opening (10 --> 12) and acidic methanolysis provides pure (+)-aspicilin (1) in 22% overall yield from 4.

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页码：2607 / 2610

页数：4

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