Stereochemical aspects of the biosynthetic routes leading to the pyrrolizidine and the quinolizidine alkaloids

Abstract

Plenary lecture delivered at the 14th International Symposium on the Chemistry of Natural Products of the International Union of Pure and Applied Chemistry, Poznan, Poland, July 9-14 1984.ABSTRACT - The regiochemistry and the stereochemistry of the biosynthetic sequences leading into retronecine from ornithine and putrescine, and into lupinine, sparteine and lupanine from lysine and cadaverine, is revealed by tracer experiments with intramolecularly doubly 13C,15N-labelled and chirally 2H-labelled substrates. The labelling patterns within the biosynthetic products were established by means of 13C NMR and 2H NMR spectroscopy. © 1985 IUPAC