Issue 14, 1990

Construction of trans-ring-fused compounds by radical cyclızation

Abstract

Enolates derived from bicyclic lactones of type (4) are alkylated with prop-2-ynylic (and allylic) bromides to give products (5) in which the unsaturated alkyl group is syn to the remaining ring-fusion hydrogen; prop-2-ynylic aldehydes can be used instead of halides and, in both cases, lactone opening with sodium phenyl selenide, esterification, and treatment with a stannane then leads to trans-ring-fused bicyclic compounds.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1990, 972-974

Construction of trans-ring-fused compounds by radical cyclızation

D. L. J. Clive, H. W. Manning and T. L. B. Boivin, J. Chem. Soc., Chem. Commun., 1990, 972 DOI: 10.1039/C39900000972

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