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

preprint
submitted on 28.05.2020 and posted on 29.05.2020 by Ronaldo Pilli, Juliana Lira Luna Freire Regueira, Luiz Fernando Silva Jr.
This work describes the total synthesis of Raputindole A (1) through a convergent approach which features: 1) an iridium-catalyzed cyclization to assembly the tricyclic core of the northern part, 2) enzymatic resolution to secure the preparation of enantiomerically pure benzylic alcohol, 3) installation of the butenyl substituent via methallylation of the corresponding benzylic carbocation and coupling of the northern and southern parts via Heck reaction. (+)-Raputindole A (1) was prepared in 10 steps (LLS) and 10% overall yield.

Funding

Conselho Nacional de Desenvolvimento Científico e Tecnoló-gico (CNPq) (1418552015-0) for research support and Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) for research grants (#2016/12096-0 and #2019/13104-5).

History

Email Address of Submitting Author

rapilli@unicamp.br

Institution

University of Campinas

Country

Brazil

ORCID For Submitting Author

0000-0002-5919-7763

Declaration of Conflict of Interest

No conflict of interest

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