SHORT SYNTHESIS OF (+)-ASPICILIN VIA ASYMMETRIC HEXAHYDROXYLATION OF A TRIENE

被引：30

作者：

SINHA, SC ^{[1
]}

KEINAN, E ^{[1
]}

机构：

[1] TECHNION ISRAEL INST TECHNOL, DEPT CHEM, IL-32000 HAIFA, ISRAEL

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 05期

关键词：

D O I：

10.1021/jo00084a006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric synthesis of the 18-membered lichen macrolide (+)-aspicilin has been achieved in 14 steps and 11% overall yield, starting from an achiral hydrocarbon, (3E)-hexadeca-1,3,15-triene. All four stereogenic carbinol centers have been introduced by three Sharpless asymmetric dihydroxylation (AD) reactions, using both AD-mix-beta and AD-mix-alpha to produce the hexol with very high regio- and enantioselectivity (epimeric excess of 88% at position 2, 96% at positions 3 and 4, and 86% at position 15).

引用

页码：949 / 951

页数：3

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