Site selective oxidation of tricyclo[3.3.1.13,7]decane (adamantane) and some of its derivatives using fungi of the genus Absidia

Tricyclo [3.3.1,l3,7]decane 1a has been converted into 1-hydroxytricyclo [3.3.1.13.7] decane 1b, tricyclo[3.3.1.13.7]decane-1,4ax-diol 4b, tricyclo[3.3.1.13.7]decane-1,3-diol 3b and to a lesser extent, 2-hydroxytricyclo [3.3.1.13,7] 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(IMI 240053) as biocatalysts. In addition, A. cylindrospora(IMI 342950) converted tricyclo[3.3.1.13.7]decane-l-carboxylic acid 1c into 4axhydroxytricyclo [3.3.1.13.7] decane-1-carboxylic acid 4c with almost complete regioselectivity. Tricyclo [3.3.1.13.7] decane derivatives 1 d–g were used as biohydroxylation substrates with A. cylindrospora(IMI 342950), giving selective biohydroxylation at the 4ax- and/or the 3-position. The 4ax-selectivity was confirmed by X-ray crystal structure determinations of 4b, 4c and 4j.