SITE-SELECTIVE OXIDATION OF TRICYCLO[3.3.1.1(3,7)]DECANE (ADAMANTANE)AND SOME OF ITS DERIVATIVES USING FUNGI OF THE GENUS ABSIDIA

Tricyclo[3.3.1.1(3,7)]decane la has been converted into 1-hydroxytricy clo[3.3.1.1(3,7)]decane 1b, tricydo[3.3.1.1(3,7)]decane-1,4ax-diol 4b, tricyclo[3.3.1.1(3,7)]decane-1,3-diol 3b and to a lesser extent, 2-hy droxytricyclo [3.3.1.1(3,7)]decane 4a (20 to 40% overall yield) using the microorganisms Absidia glauca (IMI 239693), A. cylindrospora (IMI 342950), A. spinosa (IMI 193887), A. spinosa var. biappendiculata (IMI 238610) and A. cylindrospora var, nigra (MII 240053) as biocatalysts. In addition, A. cylindrospora (IMI 342950) converted tricycle[3.3.1.1 (3,7)]decane-1-carboxylic acid 1c into x-hydroxytricyclo[3.3.1.1(3,7)] decane-1-carboxylic acid 4c with almost complete regioselectivity. Tri cyclo[3.3.1.1(3,7)]decane derivatives 1d-g were used as biohydroxylati on substrates with A. cylindrospora (IMI 342950), giving selective bio hydroxylation at the 4ax- and/or the 3-position. The 4ax-selectivity w as confirmed by X-ray crystal structure determinations of 4b, 4c and 4 j.