From Cyclic CF3-ketimines to a Family of Trifluoromethylated Nazlinine and Trypargine Analogues

An efficient (one- and two-step) synthesis of trifluoromethylated derivatives of the natural alkaloids nazlinine, trypargine, and homotrypargine was elaborated. Trifluoromethyl-substituted 5-7-membered cyclic imines were used as a masked carbonyl component in the Pictet-Spengler reaction with various tryptamines. As a result, this approach opens access to a family of alkaloid-like compounds bearing a CF3 group at position 1 of tetrahydro-β-carboline. © 2016 American Chemical Society.