A convenient synthesis of new enantiomerically pure trihydroxypyrrolizidines using L-erythrose glycosylhydroxylamine as a masked acyclic chiral nitrone

被引：22

作者：

Argyropoulos, Nikolaos G. ^{[1
]}

Gkizis, Petros ^{[1
]}

Coutouli-Argyropoulou, Evdoxia ^{[1
]}

机构：

[1] Aristotle Univ Thessaloniki, Dept Chem, Thessaloniki 54124, Greece

来源：

TETRAHEDRON | 2008年 / 64卷 / 37期

关键词：

trihydroxy pyrrolizidines; glycosylhydroxylamine; chiral nitrone; aza sugars; dipolar cycloaddition;

D O I：

10.1016/j.tet.2008.06.093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A route has been developed for the synthesis of enantiomerically pure trihydroxylated pyrrolizidines starting from L-erythrose glycosylhydroxylamine. The latter acts as a masked acyclic nitrone and reacts diastereoselectively from its Re-face with methyl acrylate to give the corresponding isoxazolidines, which after reductive N-O cleavage are recyclized to trihydroxypyrrolizidines via a Mitsunobu condensation. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：8752 / 8758

页数：7

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