A New Synthetic Route for Preparation of Enantiomers of Gossypol and Apogossypol from Racemic Gossypol

Vu Dinh Tien, Vu Van Vu and Tran Khac Vu*

School of Chemical Engineering, Hanoi University of Science and Technology, No. 1 Dai Co Viet, Hai Ba Trung, Hanoi, Vietnam

*Corresponding author: E-mail: vu.trankhac@hust.edu.vn

Abstract

The paper described the preparation of enantiomers of gossypol and apogossypol from racemic gossypol via a two-step procedure. In the first step, D-tryptophan methyl ester was used as an effective agent to resolve racemic gossypol into (–)-gossypol and (+)-gossypol. Next, the deformylation reaction of the corresponding (–)-gossypol and (+)-gossypol was conducted in sodium hydroxide solution, followed by sulfuric acid neutralization in inert atmosphere and the resulting precipitate was filtered and washed with water to give (–)-apogossypol and (+)-apgossypol, respectively in high yields and in high enantiomeric excesses.

Keywords

Racemic, (–)-Gossypol, (+)-Gossypol, D-Tryptophan methyl ester, (–)-Apogossypol, (+)-Apogossypol.

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