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

Author(s)

Regueira, Juliana L. L. F. ^{[1, 2]} ; Silva Jr, Luiz F. ; Pilli, Ronaldo A. ^[1]

Affiliation

^[1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP - Brazil

^[2] Univ Sao Paulo, Inst Chem, BR-05508000 Sao Paulo, SP - Brazil

• Document type: Journal article
• Source: ORGANIC LETTERS; v. 22, n. 16, p. 6262-6266, AUG 21 2020.
• Web of Science Citations: 0

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. (AU)

• FAPESP's process: 19/13104-5 - Planning and synthesis of inhibitors based on biological targets: the case of neglected kinases
• Grantee: Ronaldo Aloise Pilli
• Support Opportunities: Regular Research Grants