Directed Palladium-Catalyzed Acetoxylation of Indolines. Total Synthesis of <i>N</i>-Benzoylcylindrocarine
Name
directed-palladium-catalyzed-acetoxylation-of-indolines-total-synthesis-of-n-benzoylcylindrocarine.pdf
Description
Submitted version
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733.46 KB
Format
Adobe PDF
Checksum (MD5)
7e150d0f819e1aa6594658dc0c967913
Author(s)
Flynn, Kristen M
White, Kolby L
Movassaghi, Mohammad
Date Issued
March 4, 2022
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Citation
Flynn, Kristen M, White, Kolby L and Movassaghi, Mohammad. 2022. "Directed Palladium-Catalyzed Acetoxylation of Indolines. Total Synthesis of N-Benzoylcylindrocarine." The Journal of Organic Chemistry, 87 (5).
Version
Original manuscript
Abstract
We describe a palladium-catalyzed C7-acetoxylation of indolines with a range of amide directing groups. While a variety of substituents are tolerated on the indoline-core and the N1-acyl group, the acetoxylation is most sensitive to the C2- and C6-indoline substituents. The practicality of this indoline C7-acetoxylation is demonstrated using a cinnamamide substrate on a mmol scale. Several N1-acyl groups, including those present in natural alkaloids, guide C7-acetoxylation of indoline substrates over a competitive C5-oxidation. The application of this chemistry allowed for the first synthesis of N-benzoylcylindrocarine by late-stage C17-acetoxylation of N-benzoylfendleridine.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
https://doi.org/10.1021/acs.joc.1c02811
