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Acid-Promoted Redox-Annulation toward 1,2-Disubstituted-5,6-dihydropyrrolo[2,1-α]isoquinolines: Synthesis of the Lamellarin Core.

ABSTRACT: An efficient synthesis of a variety of 1,2-disubstituted-5,6-dihydropyrrolo[2,1-α]isoquinoline derivatives via an acid-promoted cyclization reaction between 1,2,3,4-tetrahydroisoquinoline (THIQ) and substituted α,β-unsaturated aldehyde derivatives is reported. This cycloaddition allows access to structurally diverse multisubstituted dihydropyrrolo[2,1-α]isoquinolines in moderate to good yields, which was the core scaffold of marine natural alkaloid lamellarins.

SUBMITTER: Hou GQ

PROVIDER: S-EPMC9608416 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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Acid-Promoted Redox-Annulation toward 1,2-Disubstituted-5,6-dihydropyrrolo[2,1-α]isoquinolines: Synthesis of the Lamellarin Core.

Hou Guo-Quan GQ Zhao Wenyan W Deng Changjiang C Dong Chunping C Wang Cheli C Liu Li L Li Jian J

ACS omega 20221014 42

An efficient synthesis of a variety of 1,2-disubstituted-5,6-dihydropyrrolo[2,1-α]isoquinoline derivatives via an acid-promoted cyclization reaction between 1,2,3,4-tetrahydroisoquinoline (THIQ) and substituted α,β-unsaturated aldehyde derivatives is reported. This cycloaddition allows access to structurally diverse multisubstituted dihydropyrrolo[2,1-α]isoquinolines in moderate to good yields, which was the core scaffold of marine natural alkaloid lamellarins. ...[more]

PMID: 36312359

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