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

doi:10.1248/cpb.56.1611

Notes

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

Author information

Keywords: sesamin, antioxidant, metabolite, lead(IV) tetraacetate, dioxirane

JOURNAL FREE ACCESS

2008 Volume 56 Issue 11 Pages 1611-1612

DOI https://doi.org/10.1248/cpb.56.1611

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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.

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