Polysubstituted dihydropyrans via the enolate Claisen rearrangement. A stereocontrolled route to C-pyranosides

…, DM Armistead, FJ Schoenen

Index: Burke, Steven D.; Armistead, David M.; Schoenen, Frank J. Journal of Organic Chemistry, 1984 , vol. 49, # 22 p. 4320 - 4322

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Citation Number: 40

Abstract

Summary: A new method for the stereoselective synthesis of dihydropyrans of a variety of substitution patterns is described, involving [3, 3]-sigmatropic reorganizations of 6-alkenyl-4- oxapyran-2-ones of general structure 1 or 3 to the product dihydropyrans (2 or 4, respectively).