NEW CHIRAL SYNTHONS FROM THE MICROBIAL OXIDATION OF BROMONAPHTHALENES

1-Bromo- and 2-bromonaphthalene were subjected to biooxidation with wh ole cells of Pseudomonas putida NCIB 9816-11. The major metabolites we re isolated and spectroscopically characterized as s-(1R,2S)-Dihydroxy -1,2-dihydro-8-bromonaphthalene 1, s-(1R,2S)-Dihydroxy-1,2-dihydro-5-b romonaphthalene 2 from 1-bromo-naphthalene and s-(1R,2S)-Dihydroxy-1,2 -dihydro-7-bromonaphthalene 8 from 2-bromonaphthalene. The absolute st ereochemistry and enantiomeric excess were determined by conversion of each metabolite to the known (-)-cis-tetrahydronaphthalene diol 6.