Stereochemistry of Products Obtained by Rearrangement and Reduction of Fencholenic Epoxides

Starting with fencholenic epoxides 8a,b and 11, investigations of the rearrangement to the corresponding ketones were carried out. Reduction of the isomeric ketones 12a,b and 13a,b afforded each diastereomeric alcohols 14, 16/17 and 15, 18/19. Diastereomeric alcohols could be obtained by reduction of 8a,b and 11 and by hydroboration/oxidation of the fencholenic compounds 7 and 22. The stereochemistry of the new compounds is described.