Tetrahedron Letters

A carbohydrate synthesis employing a photochemical decarbonylation

K Kadota, K Ogasawara

Index: Kadota, Kohei; Ogasawara, Kunio Tetrahedron Letters, 2001 , vol. 42, # 49 p. 8661 - 8664

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Citation Number: 11

Abstract

We have developed an efficient method for the preparation of the enantiopure bicyclic enones containing a bicyclo[3.2.1]octane framework, levoglucosenone 1, 1. and 2. and an isolevoglucosenone derivative 2, 3., , and 4. having an oxymethyl functionality, in both enantiomeric forms from non-carbohydrate precursors (Fig. 1). Photolysis of a monocyclic pyranone has been reported 5 to furnish an epimeric mixture of ring-contracted tetrahydrofuran derivatives with ...