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.
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From Cyclic CF3-ketimines to a Family of Trifluoromethylated Nazlinine and Trypargine Analogues.
Org Lett
September 2016
Department of Chemistry, Lomonosov Moscow State University, Moscow 119991, Russia.
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.
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