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

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

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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