Abstract
Enantiomeric pairs of cis-fused bicyclic hydroxy lactones with a p-menthane system were obtained in a several step synthesis from enantiomerically pure isomers of (+)-( R)- and (−)-( S)-pulegone. One-pot allyl-Claisen rearrangement of cis-pulegols, epoxidation of γ,δ-unsaturated p-nitrophenyl esters and acidic lactonization of epoxy esters are key synthetic steps. The structures of the compounds were confirmed by both spectroscopic and crystallographic methods.
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