Synthesis of manool-related labdane diterpenes as platelet aggregation inhibitors.
Enantioselective total synthesis of the labdane diterpene (-)-1, was achieved starting from the R-(-)-enantiomer of the Wieland-Miescher ketone. The enantiomer (+)-1 was obtained by partial synthesis via microbial transformation of sclareol. These results established that the natural compound (+)-1, a platelet aggregation inhibitor, has a normal absolute stereochemistry like that of manool. The B-norlabdane-related compound 44 was also synthesized using a novel ring contraction reaction.
Yasui
K
K
Shionogi Research Laboratories, Shionogi & Co., Ltd., Osaka, Japan.
Kawada
K
K
Kagawa
K
K
Tokura
K
K
Kitadokoro
K
K
Ikenishi
Y
Y
D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D004224:Diterpenes; D010975:Platelet Aggregation Inhibitors