Collect. Czech. Chem. Commun. 1987, 52, 1043-1051

Preparation of 3β-hydroxy-21,26,27-trinorcholesta-5,23-dien-25→22-olide and 3β-hydroxy-20-(2-furyl)-21-nor-5-pregnene derivatives

Vladimír Pouzar, Ivan Černý, Pavel Drašar, Soňa Vašíčková and Miroslav Havel

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


A mixture of 22R- and 22S-isomers of 3β-methoxymethoxy-21,26,27-trinorcholesta-5,23-dien-25→22-olide (IX) was prepared from ester I by two synthetic pathways. Lactone IX was converted into hemisuccinate XII via the intermediates X and XI. The isomer ratio in compounds IX-XII was determined by 1H NMR and CD spectra. Lactone IX was converted into 20-(2-furyl)-3β-methoxymethoxy-21-nor-5-pregnene (XIII) and further, via intermediates XIV and XV, to the β-D-glucoside XVI.