DIVERGENT ASYMMETRIC-SYNTHESIS OF ERYTHRO-3-AZIDO-1,2-EPOXIDES OR THREO-3-AZIDO-1,2-EPOXIDES FROM THE SAME 2,3-EPOXY-1-ALKANOL - A CONVENIENT SYNTHESIS OF STATINE AND ITS 3-EPIMER

被引：0

作者：

BERTELLI, L ^{[1
]}

FIASCHI, R ^{[1
]}

NAPOLITANO, E ^{[1
]}

机构：

[1] SCUOLA NORMALE SUPER PISA,I-56100 PISA,ITALY

来源：

GAZZETTA CHIMICA ITALIANA | 1993年 / 123卷 / 09期

关键词：

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A 2,3-epoxy-1-alkanol (obtained by Sharpless asymmetric epoxidation of the corresponding allylic alcohol), O-protected with a 2-methoxypropyl group, undergoes highly regioselective oxirane ring opening by attack of azide ion at C-3 to afford a monoprotected azidodiol which can be elaborated to divergently give either threo-or erythro-3-azido- 1,2-epoxide. An application to the synthesis of the natural amino acid statine, 24, and of its 3-epimer, 26, is described.

引用

页码：521 / 524

页数：4

共 12 条

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