ol8010216_si_004.pdf (4.39 MB)
Total Synthesis and Structural Confirmation of ent-Galbanic Acid and Marneral
journal contributionposted on 2008-07-03, 00:00 authored by Andrei Corbu, Manuel Perez, Maurizio Aquino, Pascal Retailleau, Simeon Arseniyadis
By capitalizing on a highly selective Claisen rearrangement, ent-galbanic acid 1 and (+)-marneral 2 have been synthesized. The relative configurations of (+)-1 and (+)-2 were unambiguously established by X-ray crystallographic analysis of the precursors 11a and 20, with the absolute configuration ensuing from their derivation from R-pulegone. In this way, the controversial issue of the configuration of galbanic acid was unequivocally settled.