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

29 May 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


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.


Raputindole A
iridium-catalyzed cyclization
indole alkaloid
total synthesis

Supplementary materials

SI raputindoleA Juliana vChemrxiv


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