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

The destructive resolution of (6aR,S)-glaucine (Ic) was accomplished by oxidation of the (6aS)-(+)-enantiomer (Ia), using Fusarium solani ATCC 12823 to yield the unnatural alkaloid (6aR)-(-)-glaucine (Ib). Eighteen cultures were examined for their ability to metabolize the (6aR)-(-)-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.