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Paper | Special issue | Vol 101, No. 2, 2020, pp.524-535
Published online, 8th October, 2019
DOI: 10.3987/COM-19-S(F)42
Synthesis of Lactonized Valoneoyl Group-Containing Ellagitannins, Oenothein C and Cornusiin B

Hitoshi Abe,* Haruka Imai, Daichi Ogura, and Yoshikazu Horino

*Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan

Abstract

The total synthesis of two ellagitannins, oenothein C and cornusiin B, which involve a lactonized valoneoyl group (LVG) in the molecules, was accomplished starting from glucose and gallic acid. Classical Ullmann coupling reactions were effective for preparation of the key intermediate, the lactonized valoneic acid derivative, which was subjected to a condensation reaction with glucose, and finally converted to the ellagitannins.