Chemical & Pharmaceutical Bulletin 2008-11-01

First chemical synthesis of antioxidative metabolites of sesamin.

Hidehito Urata, Yuka Nishioka, Takafumi Tobashi, Yasuo Matsumura, Namino Tomimori, Yoshiko Ono, Yoshinobu Kiso, Shun-Ichi Wada

Index: Chem. Pharm. Bull. 56(11) , 1611-2, (2008)

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Abstract

The first chemical synthesis of two metabolites ((1R,2S,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3,3,0]octane (SC-1) and (1R,2S,5R,6S)-2,6-bis(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3,3,0]octane (SC-2)) of sesamin was achieved by a simple two-step approach from sesamin. The approach consists of acetoxylation of the methylenedioxy moiety(ies) with lead(IV) tetraacetate and acid hydrolysis of the resulting hemiorthoester to SC-1 and SC-2.