Directed Palladium-Catalyzed Acetoxylation of Indolines. Total Synthesis of <i>N</i>-Benzoylcylindrocarine

• Main Authors: Flynn, Kristen M (Author), White, Kolby L (Author), Movassaghi, Mohammad (Author)
• Format: Article
• Language: English
• Published: American Chemical Society (ACS), 2022-03-10T20:24:00Z.
• Subjects: Article
• Online Access: Get fulltext

 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.