6.4.

Alkylation at position C-13

The conversion of palmatine to corydaline and mesocorydaline (Scheme 18) via an intermediate is an early
example of the currently well-known C-alkylation of an enamine (Jeffs, 1967). The relative proportion of
corydaline to mesocorydaline obtained from the intermediate salt apparently varies with the nature of the
reducing agent; zinc–acid systems afford predominantly corydaline while borohydride reduction is claimed to
give corydaline exclusively.

Full-size image (34K)

Scheme 18.