STEREOSPECIFIC SYNTHESIS OF THE SIDE-CHAIN OF THE STEROIDAL PLANT SEX-HORMONE OOGONIOL

The determination of the configuration at C-24 of the revised structure of oogoniol (19), a sex hormone of the water mold Achlya, was accomplished by the stereospecific synthesis of the model compounds (24S)-stigmast-5-ene-3/3, 29-diol (24) and (24fi)-stigmast-5-ene-3/3, 29-diol (53) which contain the oogoniol side chain. Diols 24 and 53 were prepared from esters 23 and 46products of the Claisen rearrangement of (23£, - and 23Z, 22S)-6/3-methoxy-3a, 5-cyclo-5a-cholest-23-en-22-ol (22 and 33) with trimethyl orthoacetate. Comparison of the proton NMR spectral data of 24 and 53 with those of oogoniol proved that the stereochemistry at C-24 of the revised structure of oogoniol is 24fi, and, therefore, that oogoniol has the stereostructure 56. © 1979, American Chemical Society. All rights reserved.