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Development of the Vinylogous Pictet-Spengler Cyclization and Total Synthesis of (±)-Lundurine?A.

ABSTRACT: A novel vinylogous Pictet-Spengler cyclization has been developed for the generation of indole-annulated medium-sized rings. The method enables the synthesis of tetrahydroazocinoindoles with a fully substituted carbon center, a prevalent structural motif in many biologically active alkaloids. The strategy has been applied to the total synthesis of (±)-lundurine?A.

SUBMITTER: Nash A

PROVIDER: S-EPMC6392010 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Development of the Vinylogous Pictet-Spengler Cyclization and Total Synthesis of (±)-Lundurine A.

Nash Aaron A Qi Xiangbing X Maity Pradip P Owens Kyle K Tambar Uttam K UK

Angewandte Chemie (International ed. in English) 20180504 23

A novel vinylogous Pictet-Spengler cyclization has been developed for the generation of indole-annulated medium-sized rings. The method enables the synthesis of tetrahydroazocinoindoles with a fully substituted carbon center, a prevalent structural motif in many biologically active alkaloids. The strategy has been applied to the total synthesis of (±)-lundurine A. ...[more]

PMID: 29663602

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