Collect. Czech. Chem. Commun. 1984, 49, 892-902

A new type of A-homo-B-norcholestane derivatives

Alexander Kasal

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


5-Bromo-6β-chloro-5α-cholestan-3β-ol (I) undergoes solvolysis to yield products of Westphalen rearrangement one of them (XXIX) undergoing further rearrangement to the A-homo-B-nor-system V. The reaction course was established by the use of suitably labeled substrates. The structures of the products and positions of the labels were determined by chemical transformations and physicochemical methods (1H, 13C NMR spectra).