Directed Palladium-Catalyzed Acetoxylation of Indolines. Total Synthesis of N‑Benzoylcylindrocarine

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 indo...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 87; no. 5; pp. 2975 - 2984
Main Authors Flynn, Kristen M, White, Kolby L, Movassaghi, Mohammad
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 04.03.2022
Subjects
Alkaloids
Catalysis
Indoles
Palladium
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Summary: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.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02811