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Total Synthesis of (+)-Raputindole A: An Iridium-Catalyzed Cyclization Approach.

ABSTRACT: This work describes the total synthesis of raputindole A (1) through a convergent approach that features (1) an iridium-catalyzed cyclization to assemble the tricyclic core of the northern part, (2) enzymatic resolution to secure the preparation of an enantiomerically pure benzylic alcohol intermediate, and (3) the installation of the isobutenyl side chain via methallylation of the corresponding benzylic carbocation and coupling of the northern and southern parts via the Heck reaction. (+)-Raputindole A (1) was prepared in 10 steps (longest linear sequence) in 3.3% overall yield.

SUBMITTER: Regueira JLLF 

PROVIDER: S-EPMC7450706 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Total Synthesis of (+)-Raputindole A: An Iridium-Catalyzed Cyclization Approach.

Regueira Juliana L L F JLLF   Silva Luiz F LF   Pilli Ronaldo A RA  

Organic letters 20200805 16

This work describes the total synthesis of raputindole A (<b>1</b>) through a convergent approach that features (1) an iridium-catalyzed cyclization to assemble the tricyclic core of the northern part, (2) enzymatic resolution to secure the preparation of an enantiomerically pure benzylic alcohol intermediate, and (3) the installation of the isobutenyl side chain via methallylation of the corresponding benzylic carbocation and coupling of the northern and southern parts via the Heck reaction. (+  ...[more]

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