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

Hisami Rodriguez-Matsui; David M. Aparicio; María L. Orea; Jorge R. Juárez; Victor Gómez-Calvario; Dino Gnecco; Alan Carrasco-Carballo; And Joel L. Terán

doi:10.20944/preprints202304.0188.v1

A peer-reviewed article of this Preprint also exists.

Rodriguez-Matsui, H.; Aparicio, D.M.; Orea, M.L.; Juárez, J.R.; Gómez-Calvario, V.; Gnecco, D.; Carrasco-Carballo, A.; Terán, J.L. Chiral Indolizinium Salts Derived from 2-Pyridinecarbaldehyde—First Diastereoselective Syntheses of (−)-1-epi-lentiginosine. Molecules 2023, 28, 3719. Rodriguez-Matsui, H.; Aparicio, D.M.; Orea, M.L.; Juárez, J.R.; Gómez-Calvario, V.; Gnecco, D.; Carrasco-Carballo, A.; Terán, J.L. Chiral Indolizinium Salts Derived from 2-Pyridinecarbaldehyde—First Diastereoselective Syntheses of (−)-1-epi-lentiginosine. Molecules 2023, 28, 3719.

Abstract

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.

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

Abstract

Keywords

Subject

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