Leland Stanford Junior University

Paul A Bartlett

William S Johnson

Estrogenic steroids are synthesized by combining under conditions favoring the formation of a trans-olefin, a .gamma.-arylpropanal with a 5,5,8,8-tetraalkoxy Wittig reagent. After hydrolysis of the gem-diethers, the resulting dioxo is internally condensed to form a cyclopentenone. The ketone is reduced to an oxy group and the resulting 2-(6'-arylhex-3'-enyl-1)cyclopent-2-en-1-ol or derivative thereof is cyclized to the .DELTA..sup.13,17 -estrene, preferably 17-alkyl-.DELTA..sup.13,17 -estrene with the A ring aromatized. After epoxidation, the 17-alkyl derivative is rearranged to form the 13-alkyl-1,3,5(10)-estratien-17-one. New compounds are provided as intermediates and final products.

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El Cerrito, CA, United States of America

Paul A Bartlett