Collect. Czech. Chem. Commun. 1985, 50, 1611-1617

Synthesis of 3β,4β-cyclopropano-19-nor-A-homosteroids

Jiří Joska, Jan Fajkoš and Jaroslav Zajíček

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


Acetolysis of the tosylate XIII, afforded the olefin XIV as the sole product. Epoxidation of the double bond gave the epoxide XV which on metal hydride reduction yielded the alcohol XVI. The structures of these products were established by spectral and chemical means and conformation of the A-homo ring in the epoxide XV is discussed on the basis of the 1H NMR spectra.