Synthesis of nor-ambreinolide from (+)-cis-abienol

Article abstract of DOI:10.1016/S0040-4020(01)89693-9

The synthesis of nor-ambreinolide (2) from cis-abienol (1) was carried out by direct treatment with OsO₄-NaIO₄ or RuO₄-NaIO₄. The oxymercuriation-demercuriation of 1 led to a mixture of 8,12-epoxylabdanes (5-17) which was also converted into nor-ambreinolide by treatment with RuO₄-NaIO₄. The formation pathways of such epoxy derivatives are discussed.