Biosynthesis of N-methylpelletierine: Vindication of a classical biogenetic concept

Article abstract of DOI:10.1021/ja00173a025

The ¹³C NMR spectrum of a sample of N-methylpelletierine (2), generated biosynthetically from sodium [1,2,3,4-¹³C₄]acetoacetate in Sedum sarmentosum Bunge, shows that the C₃ side chain of the alkaloid is derived as an intact unit from the C₄ precursor. The ¹³C NMR spectrum of a sample of the alkaloid, biosynthetically derived from sodium [1,2-¹³C₂]acetate, shows that it is the -COCH₃ unit and not the -CH₂CO- unit of the side chain that is derived from an intact acetate precursor. These results constitute evidence in support of classical biogenetic concepts and disprove three other possible routes of biosynthesis.