Chiral Indolizinium Salts Derived from 2-Pyridinecarbaldehyde-First Diastereoselective Syntheses of (-)-1- epi- lentiginosine.
Hisami Rodriguez-MatsuiDavid M AparicioMaría L OreaJorge R JuárezVíctor Gómez-CalvarioDino GneccoAlan Carrasco-CarballoJoel L TeránPublished in: Molecules (Basel, Switzerland) (2023)
The first diastereoselective synthesis of (-)-1- epi -lentiginosine from a common chiral trans -epoxyamide derived from 2-pyridincarbaldehyde is reported. This methodology involves a sequential oxirane ring opening and intramolecular 5- exo - tet cyclization of tosylate trans -epoxyalcohol to afford a diastereomeric mixture of indolizinium salts in a one-pot fashion, followed by regio- and diastereospecific pyridinium ring reduction.