Rapid Construction of a Benzo-Fused Indoxamycin Core Enabled by Site-Selective C−H Functionalizations

T. Aaron Bedell, Graham A.B. Hone, Damien Valette, Jin Quan Yu, Huw M.L. Davies, Erik J. Sorensen

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

Methods for functionalizing carbon–hydrogen bonds are featured in a new synthesis of the tricyclic core architecture that characterizes the indoxamycin family of secondary metabolites. A unique collaboration between three laboratories has engendered a design for synthesis featuring two sequential C−H functionalization reactions, namely a diastereoselective dirhodium carbene insertion followed by an ester-directed oxidative Heck cyclization, to rapidly assemble the congested tricyclic core of the indoxamycins. This project exemplifies how multi-laboratory collaborations can foster conceptually novel approaches to challenging problems in chemical synthesis.

Original languageEnglish (US)
Pages (from-to)8270-8274
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number29
DOIs
StatePublished - Jan 1 2016

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • C−H bond activation
  • natural products
  • palladation
  • rhodium carbenes
  • synthetic methods

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