Collect. Czech. Chem. Commun. 1984, 49, 306-312

New preparation of steroidal 3-hemisuccinates

Pavel Drašar, Ivan Černý, Vladimír Pouzar and Miroslav Havel

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


3-Hemisuccinates (3-(3-carboxypropanoates)) XI-XV, derived from cholesterol (I), (20R)-3β-hydroxy-21-norchola-5,22-dien-24 20-olide (II), estrone (III), (20E)-21-methoxycarbonyl-3β-hydroxypregna-5,20-diene (IV) and digitoxigenine (V), were prepared via the mixed succinates of the alcohols I-V and trichloroethanol (3-[4-(2,2,2-trichloroethoxy)-4-oxobutanoates] VI-X). The usual acylation of II and IV with succinic anhydride in pyridine failed.