The Total Synthesis of Steroids1

RB Woodward, F Sondheimer, D Taub…

Index: Woodward et al. Journal of the American Chemical Society, 1952 , vol. 74, p. 4223,4243

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Citation Number: 356

Abstract

4-Methoxytoluquinone (VI) is transformed in twenty stages into dZ-A9 (11~~ 16-bisdehydro- 20-norprogesterone(LXIV)(ca. 1 g./100 g. VI). This substance, the first totally synthetic non- aromatic steroid, is converted to methyl dl-3-ket0-A',~(~'),'~-etiocholatrienate (LXVI), and resolved. The identity of the synthetic dextrorotatory ester with a substance of the same structure derived from natural sources is shown. In view of the large body of known ...