Collect. Czech. Chem. Commun. 1980, 45, 2541-2549

Analogues of androgens with the open ring A

Alexander Kasal

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


The synthesis of the A-nor-3,5-seco analogue of dehydroepiandrosterone (VII) is based on different acylation and oxidation rates of the hydroxyl groups in A-nor-3,5-seco-5-androsten-3,17β-diol (I). The methyl ester of 5-oxo-17β-pivaloyloxy-A-nor-3,5-secoandrostan-3-oic acid (X), accessible from testosterone pivalate, was converted to 4,5-seco-analogues of testosterone and methyltestosterone (compounds XVII and XXIII).