Fungal transformation of (1R,2S,5R)-(-)-menthol by cephalosporiumaphidicola

Incubation of (1R,2S,5R)-(-)-menthol (1) with Cephalosporium aphidicola for 12 days yielded the six oxidized metabolites: 10-acetoxymenthol (2), 7-hydroxymenthol (3), 4alpha-hydroxymenthol (4), 3alpha-hydroxymenthol (5), 9-hydroxymenthol (6), and 10-hydroxymenthol (7). The structures of the novel compounds 2, 4, 5, and 7 were assigned by interpretation of their spectral data.