title: Absolute structure of panaxytriol.
abstract: 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.
authors.affiliation: Showa College of Pharmaceutical Sciences, Machida, Tokyo, Japan. ms@ac.shoyaku.ac.jp
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Satoh
authors.forename: Masayoshi
authors.initials: M
authors.lastname: Ishii
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Watanabe
authors.forename: Kimiaki
authors.initials: K
authors.lastname: Isobe
authors.forename: Taketo
authors.initials: T
authors.lastname: Uchiyama
authors.forename: Yasuo
authors.initials: Y
authors.lastname: Fujimoto
mesh_terms: 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
chemical_list: D000480:Alkynes; D053281:Enediynes; D005233:Fatty Alcohols; C057682:panaxytriol