Absolute structure of panaxytriol.
Diastereomeric mixture at C-3 of (9R,10R)-panaxytriol acetonide (3) and (9S,10S)-panaxytriol acetonide (4) were enantioselectively acetylated to give (3R)-acetates (3a-Ac, 4a-Ac) and (3S)-alcohols (3b, 4b) by enzyme mediated-acetylation using CHIRAZYME and vinyl acetate, respectively. Hydrolysis of (3R)-acetate (3a-Ac, 4a-Ac) with CHIRAZYME and phosphate buffer afforded (3R)-alcohols (3a, 4a), respectively. Deprotection of panaxytriol acetonides (3a, 3b, 4a, 4b) gave panaxatriol and its isomers, respectively. Comparison of optical rotation values of the synthetic panaxatriols with that of the natural one confirmed that the absolute configuration of panaxytriol sould be 3R,9R,10R.
Satoh
Mitsuru
M
Showa College of Pharmaceutical Sciences, Machida, Tokyo, Japan. ms@ac.shoyaku.ac.jp
Ishii
Masayoshi
M
Watanabe
Mitsuo
M
Isobe
Kimiaki
K
Uchiyama
Taketo
T
Fujimoto
Yasuo
Y
D000480:Alkynes; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D053281:Enediynes; D005233:Fatty Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013237:Stereoisomerism
D000480:Alkynes; D053281:Enediynes; D005233:Fatty Alcohols; C057682:panaxytriol