A straightforward, biomimetic synthesis of (-)-N-(a)-methylervitsine involv
ing the nucleophilic addition of the enolate derived from 2-acetylindole 1
to chiral, non-racemic pyridinium salt 2, followed by (Me2N+=CH2) I- induce
d cyclization of the resultant 1,4-dihydropyridine, with subsequent elabora
tion of the exocyclic 16-methylene and 20E-ethylidene substituents, is repo
rted.