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

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

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 FeCl3 as the sole reagent. This tandem reaction affords the c...

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Bibliographic Details
Published in:ACS omega Vol. 7; no. 43; pp. 39061 - 39070
Main Authors: Rodríguez-Álvarez, Sandra, Palazón, José M., Dorta, Rosa L.
Format: Journal Article
Language:English
Published: American Chemical Society 01-11-2022
Online Access:Get full text
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Summary: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 FeCl3 as the sole reagent. This tandem reaction affords the construction of novel fused polycyclic heterocycles with total stereochemical control.
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ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.2c04804