OPTICALLY ACTIVE FIVE-MEMBERED OXYGEN-CONTAINING RINGS. A SYNTHESIS OF (+)-ELDANOLIDE

Article abstract of DOI:10.1016/S0040-4020(01)89234-6

Stereoselective tandem Wittig-Horner - intramolecular Michael reactions followed by a retro Diels-Alder cleavage convert the optically active tricyclic lactol 1 into 2-substituted 2,5-dihydrofurans of high enantiomeric purities.These compounds are useful synthons for the obtention of natural butenolides and butanolides as illustrated by the synthesis of the pheromone (+)-eldanolide.