Resolution of racemic gossypol.
Treating racemic gossypol with chiral amine (S)-1-methylphenethyl amine gave the expected pair of diastereomeric amino condensates in which the binaphthyl nuclei racemized during further treatment. Acetylation was applied to avoid the change. On acetylation, 7 products were separated. Their structures were assigned based upon their spectroscopic data. After hydrolysis they gave optically active (+)- and (-)-gossypol correspondingly. A simple and practical method of quick separation of the diastereomers was also discussed.
D055598:Chemical Phenomena; D002621:Chemistry; D006072:Gossypol; D013237:Stereoisomerism
D006072:Gossypol