Collect. Czech. Chem. Commun. 1999, 64, 1479-1484

Epalons: Synthesis of New 16α-Carboxymethyl Derivatives

Barbora Slavíková* and Alexander Kasal

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic


The title compounds (16α-carboxymethyl-3α-hydroxy-5α-pregnan-20-one and its sodium and triethylammonium salts) were prepared from 20-oxopregna-5,16-dien-3β-yl acetate by conjugate addition of dimethyl malonate and decarboxylation. Inversion of configuration at carbon C-3 was carried out by Mitsunobu acylation with diethyl azodicarboxylate and formic acid in the presence of triphenylphosphine.

Keywords: Steroids; Epalon; 3α,5α-Tetrahydroprogesterone; GABAA-Receptor; Mitsunobu reaction; NMR spectroscopy, 1H.