Bulletin of the Chemical Society of Japan p. 2405 - 2412 (1988)
Update date:2022-08-04
Topics: Deprotection Dehydrogenation Purification Protection of Functional Groups
Matsumoto, Takashi
Imai, Sachihiko
Hayashi, Noriaki
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.
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