ol0c01943_si_001.pdf (4.17 MB)
Total Synthesis of (+)-Raputindole A: An Iridium-Catalyzed Cyclization Approach
journal contribution
posted on 2020-08-05, 22:04 authored by Juliana
L. L. F. Regueira, Luiz F. Silva, Ronaldo A. PilliThis
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.