Absolute Structure of Panaxytriol

Mitsuru Satoh; Masayoshi Ishii; Mitsuo Watanabe; Kimiaki Isobe; Taketo Uchiyama; Yasuo Fujimoto

doi:10.1248/cpb.50.126

Notes

Absolute Structure of Panaxytriol

Mitsuru Satoh, Masayoshi Ishii, Mitsuo Watanabe, Kimiaki Isobe, Taketo Uchiyama, Yasuo Fujimoto

著者情報

キーワード: panaxytriol, panax species, polyacetylene, absolute configuration, enzyme mediated-acetylation

ジャーナルフリー

2002 年 50 巻 1 号 p. 126-128

DOI https://doi.org/10.1248/cpb.50.126

詳細

抄録

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.

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