Collect. Czech. Chem. Commun. 1982, 47, 130-143

4,5-Secoanalogues of dihydrotestosterone with a cyclopropane ring in the position 5(6)

Alexander Kasal and Ladislav Kohout

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Simmons-Smith addition to substituted 3,5-seco-5-androsten-7-ols XII and XIV takes place stereospecifically, while the orientation of the cyclopropane ring is given by the configuration of the hydroxyl group in the position 7. This reaction represents the key step in the preparation of isomeric 5,6-cyclopropano-4,5-secodihydrotestosterones XXII and XXXIII.