Collect. Czech. Chem. Commun. 1990, 55, 1243-1256

Derivatives of 5α-androstan-3α- and 3β-ol with acrylate side chain

Vladimír Pouzar, Hana Chodounská, Dalibor Sameš, Pavel Drašar and Miroslav Havel

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


Hydroxy derivatives I, II, III, XVII and XX were oxidized to give the respective aldehydes IV, V, VI, XVIII and XXI which were further converted by Wittig-Horner reaction into unsaturated methyl and ethyl esters. Removal of the acetal protecting group in position 3 afforded methylesters X, XXIV and XXXVI and ethyl esters XIV, XXV and XXXVII. Compounds XXIV, XXV, XXXVI and XXXVII were converted into the corresponding hemisuccinates XXVIII, XXIX, XL and XLI and β-D-glucosides XXXII, XXXIII, XLIV and XLV.