Issue 5, 1988

Controlled Payne rearrangements of 2,3-epoxy alcohols in aprotic media: an enantioselective total synthesis of (+)-exo-brevicomin

Abstract

The catalysis of the isomerisation of primary cis-2,3-epoxy alcohols to threo-1,2-epoxy alcohols by lithium chloride in tetrahydrofuran solution is described; the more reactive terminal epoxides may be selectively trapped in situ by reaction with nucleophiles, and this methodology is used in an enantioselective synthesis of (+)-exo-brevicomin.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1988, 356-358

Controlled Payne rearrangements of 2,3-epoxy alcohols in aprotic media: an enantioselective total synthesis of (+)-exo-brevicomin

P. C. B. Page, C. M. Rayner and I. O. Sutherland, J. Chem. Soc., Chem. Commun., 1988, 356 DOI: 10.1039/C39880000356

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