Microbiological transformation of manoyl oxide derivatives by Mucor plumbeus

Biotransformations of jhanol (18-hydroxymanoyl oxide) (2), jhanidiol (1 beta, 18-dihydroxymanoyl oxide) (3), and 1-oxo-jhanol (1-oxo-18-hydroxymanoyl oxide) (4) by the fungus Mucor plumbeus have been studied. In the incubation of 2 there exists a preference for hydroxylation at C-2(alpha) (8) and C-6(beta) (9-11) and, to a lesser degree, at C-1(alpha) (7), C-11(alpha) (6), and C-11(beta) (5 and 10). In the second substrate (3), the presence of a 1 beta-hydroxyl group inhibits 6 beta- or 11-hydroxylation. Epoxidation of the; vinyl group constitutes the main reaction, with the positions 2 alpha (14) and 3 beta (15) being hydroxylated. In the incubation of 4, there was a preference for 6 beta-hydroxylation (21) or epoxidation of the vinyl group (22). Other hydroxylations observed were at the 2 alpha (19), 2 beta (20), 3 alpha (23), 3 beta (24), and 11 beta(18) positions.