Asymmetric bioreduction of racemic 5,6,7,8-tetrahydro-8-methyl-1,3-dimethoxynaphthalen-6-one to the corresponding chiral β-tetralols

The synthesis of racemic 5,6,7,8-tetrahydro-8-methyl-1,3-dimethoxynaphthalen-6-one 1 was performed and the bioreduction to the corresponding β-tetralols was studied with respect to the stereochemical course and optical purity of the products; in particular the 6S,8S enantiomer corresponding to the dimethyl derivative of the natural compound feroxidin was isolated. The biomass of: Aspergillus niger, Cladosporium cladosporioides, Candida lypolitica, Bacillus megatherium, Rhodotorula minuta, R. flava, R. rubra, Beauveria bassiana and Baker's yeast were used as biocatalysts. Relative and absolute configurations of the obtained β-tetralols were established by comparison with those of the natural feroxidin.