Bm. Fraga et al., THE BIOTRANSFORMATION OF MANOYL OXIDE DERIVATIVES BY GIBBERELLA-FUJIKUROI - THE FUNGAL EPIMERIZATION OF AN ALCOHOL GROUP, Tetrahedron, 54(22), 1998, pp. 6159-6168
The microbiological transformations of jhanol (18-hydroxymanoyl oxide)
and jhanidiol (1 beta,18-dihydroxymanoyl oxide) with the fungus Gibbe
rella fujikuroi have been studied. In the biotransformation of the fir
st compound there exists a preference for hydroxylation at C-1(a) and
in lower yield at C-11(alpha or beta), while in that of the second, wh
ich possesses a 1 beta-hydroxylation, the main reaction observed is th
e oxidation of this 1 beta-hydroxyl to an oxo group. This product is t
hen mainly reduced to the 1 alpha-alcohol or, in minor yield, hydroxyl
ated at C-11(beta), C-6(beta) and C-2(alpha). The fungal epimerization
of a hydroxyl group, as occurs in the biotransformation of the 1 beta
-alcohol of jhanidiol to the la-alcohol, is a very rare process. (C) 1
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