SELECTIVE OXYGENATION OF ADAMANTANES AND OTHER SUBSTRATES BY BEAUVERIA-SULFURESCENS

Oxygenation of N-(2-adamantyl)benzamide (7) with the fungus Beauveria sulfurescens (ATCC 7159) gave 4beta-benzamidoadamantan-1-ol (8), whose structure was determined by X-ray crystallography. Oxygenation of N-methyl-N-(4-methyleneadamant-1-yl)benzamide (9) gave two products, the beta-epoxide 10 and the 5-hydroxy beta-epoxide 11, the latter structure determined by X-ray crystallography. Oxygenation of 4-methylene-l-(p-toluenesulfonyl)piperidine (12) gave 4-hydroxy-4-(hydroxymethyl)-l-(p-toluenesulfonyl)piperidine (14) and of 4-piperidinoacetophenone (13) gave 4-(4-hydroxypiperidino)acetophenone (15).