Synthesis of 2-methyl-D-erythritol via epoxy ester-orthoester rearrangement |
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Authors: | Giner José-Luis Ferris William V Mullins Joseph J |
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Institution: | Department of Chemistry, State University of New York-ESF, Syracuse, New York 13210, USA. jlginer@syr.edu |
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Abstract: | The biomimetic epoxy esterbond]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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