Chemistry of labdanediol from Cistus ladaniferus, L. synthesis of 12-Nor-ambreinolide and α and β-levantenolides

Article abstract of DOI:10.1016/S0040-4020(01)88343-5

Labdanediol, 2, the major component of the neutral part of Cistus ladaniferus L, was transformed into 12-nor-ambreinolide, precursor of ambrox, in three steps with an overall yield of 70%. Molecular modelling techniques have been used to determine the stereochemistry of the byproducts of these reactions. The selenylation and elimination reactions of α and βlevantanolides, obtained from labdanediol, 2, were used to synthetise α and β-levantenolides.