An expedient route for the practical preparation of optically active (−)-gossypol |
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Institution: | State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China |
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Abstract: | A simple and practical procedure has been developed for the resolution of racemic gossypol. The commercially available l-amino acid esters have been employed as the resolving agents with the l-tryptophan methyl ester (l-Trp-OMe) as the best reagent of choice. The individual diastereoisomeric gossypol adducts derived from l-Trp-OMe are readily separated by a simple filtration step to give the (−)-diastereoisomeric adduct, and its (+)-diastereoisomeric adduct can be easily obtained by simple evaporation of the mother liquor. Acid hydrolysis of the separated adduct gave (−)-gossypol and (+)-gossypol, respectively, in high chemical yields (quantitatively) and in high enantiomeric excesses (>95%). |
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