Summary
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1.
Two improved variants of the synthesis of the methyl ether of D-homoestrone (IV) were developed. In the first variant, the ketal of the methyl ether of 8,9-dehydro-D-homoestrone (VI) is reduced with potassium in liquid ammonia to the ketal of (IV) [(VII)], which on hydrolysis gives the ketone (IV). In the second variant the methyl ether of 8,9-dehydro-D-homoestrone (VIII) is reduced directly with potassium in liquid ammonia to the ketone (IV).
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2.
An investigation was made of the conditions for the condensation of 1,2,3,4-tetrahydro-6-methoxy-1-vinyl-2-naphthol (I) with 2-methyl-1,3-cyclohexanedione. The best catalyst was found to be Triton B, and the best solvent found was p-xylene.
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Literature cited
S. N. Ananchenko, V. N. Leonov, A. V. Platonova, and I. V. Torgov, Dokl. AN SSSR135, 73 (1960).
V. M. Rodionov, Izv. AN SSSR, Otd. khim. n.1948, 251.
I. N. Nazarov, I. V. Torgov, and G. P. Verkholetova, Dokl. AN SSSR112, 1067 (1957).
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Research student at the Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai.
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Ananchenko, S.N., Jeng-o, T. & Torgov, I.V. Variants of the total synthesis of estrone on the basis of 6-methoxy-1-vinyl-2-naphthol and 2-methyl-1,3-cyclohexanedione. Russ Chem Bull 11, 275–278 (1962). https://doi.org/10.1007/BF00908033
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DOI: https://doi.org/10.1007/BF00908033