The biotransformation of tricyclo[2.2.1.02,6]hept‐3‐yl N‐phenylcarbamate (8) by a standard procedure using Beauveria bassiana gave a 7:1 mixture of optically active exo,exo‐ and exo,endo‐5‐hydroxytricyclo[2.2.1.02,6]hept‐3‐yl N‐phenylcarbamates 15 and 16 in 19% isolated yield. No ring opening of the three‐membered ring was observed. Substitution with a fluorine atom at the 5‐endo‐ or 5‐exo‐position prevented hydroxylation of any alicyclic position of the molecules, p‐hydroxylation of the aromatic ring occurring to a small extent instead. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)