Collect. Czech. Chem. Commun. 1984, 49, 1039-1050

Synthesis of 17β-[4-(1,3-thiazolyl)]androstane 3β-hemisuccinate and glycoside

Pavel Drašar, Vladimír Pouzar, Ivan Černý, Jorga Smolíková and Miroslav Havel

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


The protected 20(21)-en-20-ol ether III was oxidized with N-methylmorpholine N-oxide monohydrate and osmium tetroxide to give the hydroxy ketone IV which was converted into the bromo derivative VIII via the mesylate VI. Hantzsch reaction of the bromo ketone VIII with ethyl thioxamate afforded the thiazole XI whose hemisuccinate XIII and glycoside XV were prepared.