Stereospecific synthesis of the side chain of the steroidal plant sex hormone oogoniol

JR Wiersig, N Waespe-Sarcevic…

Index: Wiersig,J.R. et al. Journal of Organic Chemistry, 1979 , vol. 44, p. 3374 - 3382

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Citation Number: 54

Abstract

The determination of the configuration at (2-24 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@, 29-diol (24) and (24R)-stigmast-5-ene-3P, 29-diol (53) which contain the oogoniol side chain. Diols 24 and 53 were prepared from esters 23 and 46-products of the Claisen rearrangement of (23E,-and 232,229)-6~- ...