Incorporation of the enantiomeric [1-2H]cadaverines into the quinolizidine alkaloid (–)- anagyrine in Anagyris foetida

Abstract

The labelling patterns in (–)-anagyrine 13 derived biosynthetically from (R)- and (S)-[1-²H]cadaverine 5 and 6, respectively in Anagyris foetida have been established by ²H NMR spectroscopy. Comparison of the composite labelling pattern 14 with that 11 published for (+)-sparteine has distinguished between two possible pathways for conversion of a tetracyclic intermediate into (–)-anagyrine.