Microbial Reduction of Naphthoxypropionic Acids.

Racemic 2- (1-naphthoxy) propionic acid ((±) -1) and 2- (2-naphthoxy) propionic acid ((±) -4) were subjected to microbial reduction and simultaneous resolution with Glomerella cingulata (Malus and Prunus strains), Gloeosporium olivarum (G. olivarum) and Gloeosporium laeticolor (G. laeticolor), yielding (S) - (+) -2- (1-naphthoxy) propanol ((S) -2) and (R) - (+) -2- (2-naphthoxy) - propanol ((R) -5), and leaving (R) - (-) -2- (1-naphthoxy) propionic acid ((R) -1) and (S) - (-) -2- (2- naphthoxy) propionic acid ((S) -4), respectively. The optical purity of (S) - (+) -2- (1-naphthoxy) - propanol ((S) -2) reached 92% and over 99% ee when fermented with G. olivarum and Glomerella cingulata (Malus strain), respectively.