A short-step synthesis of 14,15-dinoreudesmanolides using intramolecular cyclization of an allylsilane
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 519-524
- https://doi.org/10.1039/p19900000519
Abstract
14,15-Dinoreudesman-12,6-olides, α-methylene-γ-lactones fused to a trans-decalin ring with all three possible stereochemistries, were synthesized from a simple dialdehyde monoacetal via intramolecular cyclization of ethyl 5-(2-formylcyclohexyl)-2-(trimethylsilylmethyl)pent-2-enoate. The stereoselectivity of the cyclization reaction is described.This publication has 3 references indexed in Scilit:
- Studies on the syntheses of sesquiterpene lactones. 10. Improved syntheses of (+)-tuberiferin and the related .alpha.-methylene-.gamma.-lactones and their biological activitiesThe Journal of Organic Chemistry, 1987
- Allylsilane-initiated cyclopentane annulationsThe Journal of Organic Chemistry, 1986
- Biological activities of sesquiterpene lactonesPhytochemistry, 1976