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

ABSTRACT: 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.

SUBMITTER: Rodriguez-Alvarez S

PROVIDER: S-EPMC9631894 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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

Rodríguez-Álvarez Sandra S Palazón José M JM Dorta Rosa L RL

ACS omega 20221017 43

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<sub>3</sub> as the sole reagent. This tandem reaction affords the construction of novel fused polycyclic heterocycles with total stereochemical control. ...[more]

PMID: 36340113

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