Selective Oxygenation of Adamantanes and Other Substrates by Beauveria sulfurescens

Article abstract of DOI:10.1021/jo00052a039

Oxygenation of N-(2-adamantyl)benzamide (7) with the fungus Beauveria sulfurescens (ATCC 7159) gave 4β-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 β-epoxide 10 and the 5-hydroxy β-epoxide 11, the latter structure determined by X-ray crystallography.Oxygenation of 4-methylene-1-(p-toluenesulfonyl)piperidne (12) gave 4-hydroxy-4-(hydroxymethyl)-1-(p-toluenesulfonyl)piperidine (14) and of 4-piperidinoacetophenone (13) gave 4-(4-hydroxypiperidino)acetophenone (15).