Formation of trans ring-fused compounds by an alkylation-radical cyclization sequence

DLJ Clive, HW Manning, TLB Boivin…

Index: Clive, Derrick L. J.; Manning, Hartford W.; Boivin, Taryn L. B.; Postema, Maarten H. D. Journal of Organic Chemistry, 1993 , vol. 58, # 24 p. 6857 - 6873

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Citation Number: 29

Abstract

Enolates derived from bicyclic lactones of type 1 (Scheme I) can be alkylated with 2- propynylic halides to give products 2, in which the unsaturated alkyl group is syn to the adjacent ring-fusion hydrogen. Reaction of 2 with sodium phenyl selenide and then with diazomethane produces esters 3, and these give trans ring-fused bicyclic compounds 4 when treated with triphenyltin hydride in the presence of a radical initiator. The bicyclic ...