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Construction of trans-ring-fused compounds by radical cyclızation

1990; Royal Society of Chemistry; Issue: 14 Linguagem: Inglês

10.1039/c39900000972

2050-5639

Derrick L. J. Clive, Hartford W. Manning, Taryn L. B. Boivin,

Advanced Synthetic Organic Chemistry

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.