Biosynthesis of lycopodine. Incorporation of Δ1-piperideine and of pelletierine

Abstract

The biogenetic hypothesis that the Lycopodium alkaloids are modified dimers of pelletierine (2, 3) was tested experimentally in Lycopodiumtristachyum, Pelletierine is indeed incorporated into lycopodine, but only one pelletierine unit entered the alkaloid, rather than two units, as predicted. The hypothesis thus requires modification.Δ1-Piperideine serves as a specific precursor of lycopodine. Two Δ1-piperideine moieties are incorporated in such a way that the identity of C-2 and -6 of each of the precursor units is maintained.