Iron Trichloride-Mediated Cascade Reaction of Aminosugar Derivatives for the Synthesis of Fused Tetrahydroisoquinoline–Tetrahydrofuran Systems

[Image: see text] A method to obtain tetrahydroisoquinolines (THIQs) fused to tetrahydrofuran rings from aminosugar derivatives has been developed. The procedure relies on a key deprotection of benzyl ethers followed by a double-cyclization sequence, using FeCl(3) as the sole reagent. This tandem re...

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Autores principales: Rodríguez-Álvarez, Sandra, Palazón, José M., Dorta, Rosa L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9631894/
https://www.ncbi.nlm.nih.gov/pubmed/36340113
http://dx.doi.org/10.1021/acsomega.2c04804
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author Rodríguez-Álvarez, Sandra
Palazón, José M.
Dorta, Rosa L.
author_facet Rodríguez-Álvarez, Sandra
Palazón, José M.
Dorta, Rosa L.
author_sort Rodríguez-Álvarez, Sandra
collection PubMed
description [Image: see text] A method to obtain tetrahydroisoquinolines (THIQs) fused to tetrahydrofuran rings from aminosugar derivatives has been developed. The procedure relies on a key deprotection of benzyl ethers followed by a double-cyclization sequence, using FeCl(3) as the sole reagent. This tandem reaction affords the construction of novel fused polycyclic heterocycles with total stereochemical control.
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spelling pubmed-96318942022-11-04 Iron Trichloride-Mediated Cascade Reaction of Aminosugar Derivatives for the Synthesis of Fused Tetrahydroisoquinoline–Tetrahydrofuran Systems Rodríguez-Álvarez, Sandra Palazón, José M. Dorta, Rosa L. ACS Omega [Image: see text] A method to obtain tetrahydroisoquinolines (THIQs) fused to tetrahydrofuran rings from aminosugar derivatives has been developed. The procedure relies on a key deprotection of benzyl ethers followed by a double-cyclization sequence, using FeCl(3) as the sole reagent. This tandem reaction affords the construction of novel fused polycyclic heterocycles with total stereochemical control. American Chemical Society 2022-10-17 /pmc/articles/PMC9631894/ /pubmed/36340113 http://dx.doi.org/10.1021/acsomega.2c04804 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Rodríguez-Álvarez, Sandra
Palazón, José M.
Dorta, Rosa L.
Iron Trichloride-Mediated Cascade Reaction of Aminosugar Derivatives for the Synthesis of Fused Tetrahydroisoquinoline–Tetrahydrofuran Systems
title Iron Trichloride-Mediated Cascade Reaction of Aminosugar Derivatives for the Synthesis of Fused Tetrahydroisoquinoline–Tetrahydrofuran Systems
title_full Iron Trichloride-Mediated Cascade Reaction of Aminosugar Derivatives for the Synthesis of Fused Tetrahydroisoquinoline–Tetrahydrofuran Systems
title_fullStr Iron Trichloride-Mediated Cascade Reaction of Aminosugar Derivatives for the Synthesis of Fused Tetrahydroisoquinoline–Tetrahydrofuran Systems
title_full_unstemmed Iron Trichloride-Mediated Cascade Reaction of Aminosugar Derivatives for the Synthesis of Fused Tetrahydroisoquinoline–Tetrahydrofuran Systems
title_short Iron Trichloride-Mediated Cascade Reaction of Aminosugar Derivatives for the Synthesis of Fused Tetrahydroisoquinoline–Tetrahydrofuran Systems
title_sort iron trichloride-mediated cascade reaction of aminosugar derivatives for the synthesis of fused tetrahydroisoquinoline–tetrahydrofuran systems
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9631894/
https://www.ncbi.nlm.nih.gov/pubmed/36340113
http://dx.doi.org/10.1021/acsomega.2c04804
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