Synthesis of (1S,2R,12S)-2-hydroxy-11-dihydroneocembrene

Abstract Aiming at the asymmetric total synthesis of trinervitane-type diterpenes, an efficient synthetic route to the title compound was explored starting from the THP ether of pivaloyloxy geraniol 11e . The coupling reaction with Grignard reagent 14 bearing the stereogenic carbon proceeded smoothly to give the THP ether of (11 S )-10-dihydrogeranylgeraniol 10 . Conversion to the corresponding acid chloride through the intermediate 9 , followed by cyclization, afforded the dihydrocembrene derivative 8 , from which the title compound 7 was prepared.