144969-67-5Relevant articles and documents
The Synthesis of Methyl (15S)-16-Hydroxydehydroabietate and Its (15R)-Epimer
Matsumoto, Takashi,Imai, Sachihiko,Hayashi, Noriaki
, p. 2405 - 2412 (1988)
In order to elucidate the absolute configuration of C-15 in natural 16-hydroxydehyroabietic acid, a metabolite of (+)-dehydroabietic acid in rabbits, methyl (+)-dehydroabietate was transformed into methyl (15S)-16-hydroxy-8,11,13-abietatrien-18-oate (3a) and its (15R)-epimer (3b).The synthetic 3a was identical with a methyl ester derived from the natural acid.Thus, the absolute configuration of C-15 in natural 16-hydroxydehydroabietic acid was conclusively assigned as an S-configuration.