Microbial transformations of galanthamin-precursors

Summary Galanthamin is a medical important alkaloid. Its chemical synthesis gives a racemic product in low yields. Starting with a belladinderivative an enzymatic ring closure should lead exclusively to a chiral product possibly with the native structure. Although this reactions type is unknown in preparative biotransformations a large number of microorganisms were tested, unfortunately without success. On the other hand in the screen transformation products were found resulting from specific dealkylations of the subtrate. The type of metabolite formed was dependent on the fungi utilized for the transformation. Additionally two N-oxides were formed by Septomyxa affinis, one in good yield. It is possible that the chirality of this compound can direct the ring closure preferentially or exclusively to the desired stereoisomer of narwedine.