Thermal/Hyperbaric Heterocycloaddition of 1,4-Dialkoxy-1,3-dienes: The de novo (E,Z) Way to Sugars
- 23 October 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (23), 8054-8062
- https://doi.org/10.1021/jo0204193
Abstract
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.Keywords
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