SYNTHESIS OF GALANTHAMINE AND RELATED ALKALOIDS - NEW APPROARCHES. I.

Article abstract of DOI:10.1016/S0040-4020(01)81012-7

Modifications of protecting groups and of the oxidative coupling conditions led to pure crystalline intermediates in the synthesis of galanthamine derivatives and gave dienone A in better yields than reported before.The E-configuration of amide 3' in crystalline state has been determined by X-ray diffraction.Streptomyces affinis 6737 reduces A to the optically active (-)-epigalanthamine derivative C, whose absolute configuration was determined by Bijvoet's method.Nematospora corylii CBS 2608 reduces to racemic B.With Ashbya gossypii IFO 1355 a mixture of racemic B and of optically active C is obtained.Some other microbial transformations are described.