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| - Synthesis of 2-Methyl-d-erythritol via Epoxy Ester−OrthoesterRearrangement
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| - The biomimetic epoxy ester−orthoester rearrangement has been applied to a new synthesis of2-methyl-d-erythritol, a branched five-carbon sugar of importance to the deoxyxylulose pathway ofisoprenoid biosynthesis. The intermediate orthoacetate is one of the few [2.2.1]-orthoesters to havebeen reported. Labeling studies with O-18 indicated that this reaction proceeds exclusively via a5-exo cyclization. NMR analysis of chiral esters indicated an ee of 87% for the starting epoxide andan ee of 86% for the product. This route represents a rapid and convenient method for the synthesisof 2-methyl-d-erythritol and is expected to be useful for generating isotopically labeled intermediatesfor biochemical studies.
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