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1-(Z)-Alkoxy-4-(E)-methoxybutadiene derivatives have been reacted with ethylgyoxylate and diethyl ketomalonate under thermal or hyperbaric conditions. They provide, with a total regioselectivity and fair to total endoselectivities, the expected dihydropyranic cycloadducts. Three of those pseudo-glycals have been converted in a few classical steps (deprotection, reduction, and dihydroxylation) into (racemic) allose, mannose, and gullose derivatives. The order of these three steps has a direct influence on the efficiency of the transformation and determines the stereochemistry of the final sugar.

Type

Journal article

Journal

J Org Chem

Publication Date

15/11/2002

Volume

67

Pages

8054 - 8062

Keywords

Aldehydes, Alkadienes, Carbohydrates, Pressure, Stereoisomerism, Temperature