Microbial transformations of glaucine

Abstract

Microbial transformation experiments were conducted with the aporphine alkaloid glaucine. Small-scale screening experiments provided a number of micro-organisms which produced three metabolites. In preparative scale studies, Streptomyces griseus(Ul 1158) produced norglaucine (4) and 2-O-demethylglaucine (6)(predicentrine) in 11 and 14% yield, respectively. Fusarium solani(ATCC 12823) produced didehydroglaucine (3) and a norapor-phinone (10)(an artefact) in 60 and 21% yield, respectively. With racemic glaucine, F. solani preferentially dehydrogenated (+)-(S)-glaucine, and unchanged, optically enriched (–)-(R)-glaucine was recovered from fermentations. N- and O-dealkylation did not occur in stereoselective fashion.