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

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 dias...

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Autores principales: Rodriguez-Matsui, Hisami, Aparicio, David M., Orea, María L., Juárez, Jorge R., Gómez-Calvario, Victor, Gnecco, Dino, Carrasco-Carballo, Alan, Terán, Joel L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10180032/
https://www.ncbi.nlm.nih.gov/pubmed/37175128
http://dx.doi.org/10.3390/molecules28093719
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author Rodriguez-Matsui, Hisami
Aparicio, David M.
Orea, María L.
Juárez, Jorge R.
Gómez-Calvario, Victor
Gnecco, Dino
Carrasco-Carballo, Alan
Terán, Joel L.
author_facet Rodriguez-Matsui, Hisami
Aparicio, David M.
Orea, María L.
Juárez, Jorge R.
Gómez-Calvario, Victor
Gnecco, Dino
Carrasco-Carballo, Alan
Terán, Joel L.
author_sort Rodriguez-Matsui, Hisami
collection PubMed
description 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.
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spelling pubmed-101800322023-05-13 Chiral Indolizinium Salts Derived from 2-Pyridinecarbaldehyde—First Diastereoselective Syntheses of (−)-1-epi-lentiginosine Rodriguez-Matsui, Hisami Aparicio, David M. Orea, María L. Juárez, Jorge R. Gómez-Calvario, Victor Gnecco, Dino Carrasco-Carballo, Alan Terán, Joel L. Molecules Communication 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. MDPI 2023-04-25 /pmc/articles/PMC10180032/ /pubmed/37175128 http://dx.doi.org/10.3390/molecules28093719 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Rodriguez-Matsui, Hisami
Aparicio, David M.
Orea, María L.
Juárez, Jorge R.
Gómez-Calvario, Victor
Gnecco, Dino
Carrasco-Carballo, Alan
Terán, Joel L.
Chiral Indolizinium Salts Derived from 2-Pyridinecarbaldehyde—First Diastereoselective Syntheses of (−)-1-epi-lentiginosine
title Chiral Indolizinium Salts Derived from 2-Pyridinecarbaldehyde—First Diastereoselective Syntheses of (−)-1-epi-lentiginosine
title_full Chiral Indolizinium Salts Derived from 2-Pyridinecarbaldehyde—First Diastereoselective Syntheses of (−)-1-epi-lentiginosine
title_fullStr Chiral Indolizinium Salts Derived from 2-Pyridinecarbaldehyde—First Diastereoselective Syntheses of (−)-1-epi-lentiginosine
title_full_unstemmed Chiral Indolizinium Salts Derived from 2-Pyridinecarbaldehyde—First Diastereoselective Syntheses of (−)-1-epi-lentiginosine
title_short Chiral Indolizinium Salts Derived from 2-Pyridinecarbaldehyde—First Diastereoselective Syntheses of (−)-1-epi-lentiginosine
title_sort chiral indolizinium salts derived from 2-pyridinecarbaldehyde—first diastereoselective syntheses of (−)-1-epi-lentiginosine
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10180032/
https://www.ncbi.nlm.nih.gov/pubmed/37175128
http://dx.doi.org/10.3390/molecules28093719
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