A Total Asymmetric Synthesis of (-)-Suaveoline.

A new total synthesis of (–)-suaveoline from L-tryptophan is reported (overall yield ca. 14%); key steps include a high yielding cis-specific Pictet–Spengler reaction, a one-pot Horner–Wadsworth–Emmons/alkylation procedure, a vinylogous Thorpe cyclization and the direct formation of a pyridine from a 1,5-dinitrile.