Intermediate in the synthesis of estrone

Details Intermediate in the synthesis of estrone Intermediate in the synthesis of estrone

1976-09-24

1978-09-26

Myers, Jane S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

542400, 26023955R, 260397, 2603973, 2603974, 2603975, 2604888R, 260590R, 260590C, 260609R, 260611A, 260613D, 26034852, 560255, 568807, 2603403, C07C 6978

Patent

active

041172345

ABSTRACT:
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.

REFERENCES:
patent: 3598845 (1971-08-01), Johnson

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