Chiral Indolizinium Salts Derived from 2-Pyridinecarbaldehyde. First Diastereoselective Syntheses of (–)-1-Epi-Lentiginosine

Autor: Hisami Rodriguez-Matsui, David M. Aparicio, María L. Orea, Jorge R. Juárez, Victor Gómez-Calvario, Dino Gnecco, Alan Carrasco-Carballo, And Joel L. Terán
Rok vydání: 2023
Předmět:
DOI: 10.20944/preprints202304.0188.v1
Popis: The first diastereoselective synthesis of (–)-1-epi-lentiginosine stars 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 tras-epoxyalcohol to afford a diastereomeric mixture of indolizinium salts in a one-pot fashion, followed by regio- and diastereospecific pyridinium ring reduction.
Databáze: OpenAIRE