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

AUTOR(ES)

Davis, Patrick J.

RESUMO

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.

Documentos Relacionados

• Preparative-scale purification of RNA using an efficient method which combines gel electrophoresis and column chromatography.
• Organic Synthesis: New Vistas in the Brazilian Landscape
• Stereospecific oxidation of (R)- and (S)-1-indanol by naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4.
• Formation of trichothecenes by Fusarium solani var. coeruleum and Fusarium sambucinum in potatoes.
• Zr[bis(salicylidene)ethylenediaminato]-mediated Baeyer–Villiger oxidation: Stereospecific synthesis of abnormal and normal lactones