Stereocontrolled Conversion of Allylic Alcohols Into VicinalCis-Diols: New Syntheses of Methyl α-L-Digitoxoslde and Methyl 2-Deoxy-α-L-Fucoside
- 1 March 1985
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 4 (1) , 1-14
- https://doi.org/10.1080/07328308508062945
Abstract
A synthetic process is outlined in which an allylic alcohol is converted into its primary urethane derivative, which is then subjected to iodonium ion induced cyclization to give a single iodo-carbonate. The carbonate is then deiodinated reductively and hydrolyzed to afford the vicinal diol. By use of this process the two title sugars have been prepared from methyl 2.3.6-trideoxv-α-L-ervthro-hex-2-enopvranoside and its α-L-threo counterpart.This publication has 14 references indexed in Scilit:
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