Synthesis, Isolation, and Characterization of the Cis and Trans Isomers of Steroidal 20-Hydroxy-17(20)-en-21-aldehydes

Article abstract of DOI:10.1021/jo00267a019

The cis- and trans-17(20)-ene-20-hydroxy-21-aldehydes (enol aldehydes) along with their acetate derivatives were prepared from the parent ketols, cortisol, cortisone, 11-deoxycortisol, prednisolone, and prednisone by reaction with zinc acetate in glacial acetic acid.Separation and isolation of the pure isomers was accomplished for the first time by reversed-phase high-performance liquid chromatography.Stereochemical assignments were based on unequivocal partial syntheses.Significant differences in the ultraviolet spectra, optical rotatory properties, and nuclearmagnetic spectra of the cis and trans isomers were found.The availability of pure enol aldehydes will make possible studies centering on their possible role as intermediates in the metabolism of the ketol side chain.