A NATURAL PRODUCT WAS SHOWN TO BE OF LOW OPTICAL PURITY: SYNTHESIS OF (2S,5R,6E,8E)-2,5-EPOXY-6,8-MEGASTIGMADIENE, ITS (6Z,8E)-ISOMER AND (2S,6R,7S,8E)-2,7-EPOXY-4,8-MEGASTIGMADIENE, THE CONSTITUENTS OF OSMANTHUS ABSOLUTE

Article abstract of DOI:10.1016/S0040-4020(01)90549-6

The title compounds were synthesized from (S)-3-hydroxy-2,2-dimethylcyclohexanone. (6E,8E)-2,5-Epoxy-6,8-megastigmadiene isolated as a minor constituent of Osmanthus absolute was shown to be of only ca. 11percent e.e. enriched in (2S,5R)-(+)-isomer.