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Issue 23, 1997
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Parlaying C–O chirality into C–C chirality: improving the cost/benefit ratio of carbohydrate templates

Abstract

Use of sugars as chirons for complex carbocyclic targets requires that C–O chirality be transmuted into C–C chirality. The cost/benefit ratio in such syntheses is one index of efficiency. For example, the process involving oxidation of a secondary alcohol followed by methylenation and hydrogenation gives, at best, a 1:1 ratio. The aim of lowering this ratio has been a feature of our synthetic studies, some of which are described in this article. Among other things, the studies show that the stereochemistry of pendant, off-template mixed acetals can direct the stereo- and regio-selectivity choices (e.g. 5-exo-trig versus 6-exo-trig) in radical cyclization reactions.

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Article type: Paper
DOI: 10.1039/A704040G
Chem. Commun., 1997, 2251-2257

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    Parlaying C–O chirality into C–C chirality: improving the cost/benefit ratio of carbohydrate templates

    J. Cristobal Lopez and B. Fraser-Reid, Chem. Commun., 1997, 2251
    DOI: 10.1039/A704040G

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