Synthesis of 2-methyl-D-erythritol via epoxy ester-orthoester rearrangement

被引：29

作者：

Giner, JL ^{[1
]}

Ferris, WV

Mullins, JJ

机构：

[1] SUNY, ESF, Dept Chem, Syracuse, NY 13210 USA

[2] Le Moyne Coll, Dept Chem, Syracuse, NY 13214 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 14期

关键词：

D O I：

10.1021/jo020168y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The biomimetic epoxy ester-orthoester rearrangement has been applied to a new synthesis of 2-methyl-D-erythritol, a branched five-carbon sugar of importance to the deoxyxylulose pathway of isoprenoid biosynthesis. The intermediate orthoacetate is one of the few [2.2.1]-orthoesters to have been reported. Labeling studies with o-18 indicated that this reaction proceeds exclusively via a 5-exo cyclization. NMR analysis of chiral esters indicated an ee of 87% for the starting epoxide and an ee of 86% for the product. This route represents a rapid and convenient method for the synthesis of 2-methyl-D-erythritol and is expected to be useful for generating isotopically labeled intermediates for biochemical studies.

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页码：4856 / 4859

页数：4

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