STUDIES ON THE TERPENOIDS AND RELATED ALICYCLIC COMPOUNDS XXII STEREOCHEMICAL STUDY ON THE ANGULAR HYDROXYLATION OF POLYCYCLIC KETONES USING BENZENESELENINIC ANHYDRIDE

Article abstract of DOI:10.1016/S0040-4020(01)92418-4

Introduction of an OH group to the tertiary carbon of simple ketones (1, 2 and 6), furanoeremophilane-type ketones (12-19), and tricyclic ketones (20-22) by the use of benzeneseleninic anhydride is described. 10β-Hydroxy compounds were obtained in the case of 12-14, and 20-22. 10α-Hydroxy compounds were obtained in the case of 15 and 16.In the hydroxylation reaction of polycyclic ketones using benzeneseleninic anhydride, the results suggest that the thermodynamically more stable product was usually produced as the major product.