Chiral Indolizinium Salts Derived from 2-Pyridinecarbaldehyde-First Diastereoselective Syntheses of (-)-1- epi- lentiginosine

  • Molecules. 2023 Apr 25;28(9):3719. doi: 10.3390/molecules28093719.
Hisami Rodriguez-Matsui  1 ,  David M Aparicio  1 ,  María L Orea  1 ,  Jorge R Juárez  1 ,  Victor Gómez-Calvario  1 ,  Dino Gnecco  1 ,  Alan Carrasco-Carballo  2 ,  Joel L Terán  1
Affiliations
  • 1. Centro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Edif. IC9 Complejo de Ciencias, C.U., Puebla 72570, Mexico.
  • 2. Laboratorio de Elucidación y Síntesis en Química Orgánica, Benemérita Universidad Autónoma de Puebla, C.U., Puebla 72570, Mexico.
PMID: 37175128 DOI: 10.3390/molecules28093719
Abstract

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.

Keywords
(−)-1-epi-lentiginosine; diastereoselective synthesis; indolizinium salts; trans-epoxyamides.
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