Incorporation of chiral [1-2H]cadaverines into the quinolizidine alkaloids sparteine, lupanine, and angustifoline

Abstract

² H N.m.r. Spectroscopy has been used to establish the labelling patterns in sparteine (3), lupanine (5), and angustifoline (7), derived biosynthetically from (R)-[1-²H]-(8) and (S)[1-²H]-cadaverine (9); the presence of ²H at C-17 in these three alkaloids from the former precursor (8) demonstrates that 17-oxosparteine cannot be an intermediate in quinolizidine alkaloid biosynthesis.