Microbiological Systems in Organic Synthesis: Preparative-Scale Resolution of ( R S )-Glaucine by Fusarium solani and Stereospecific Oxidation of ( R )-(−)-Glaucine by Aspergillus flavipes

Abstract

The destructive resolution of (6a R , S )-glaucine (Ic) was accomplished by oxidation of the (6a S )-(+)-enantiomer (Ia), using Fusarium solani ATCC 12823 to yield the unnatural alkaloid (6a R )-(−)-glaucine (Ib). Eighteen cultures were examined for their ability to metabolize the (6a R )-(−)-enantiomer (Ib), and Aspergillus flavipes ATCC 1030 was found to catalyze the stereoselective oxidation of this substrate to didehydroglaucine. Thus, it has been demonstrated that “ R ” and “ S ” organisms exist with regard to the oxidation of aporphines to didehydroaporphines.