title: Rapid Construction of a Benzo-Fused Indoxamycin Core Enabled by Site-Selective C-H Functionalizations.
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.
authors.affiliation: Frick Chemistry Laboratory, Department of Chemistry, Princeton University, Washington Road, Princeton, NJ, 08544, USA.
authors.forename: T Aaron
authors.initials: TA
authors.lastname: Bedell
authors.affiliation: Frick Chemistry Laboratory, Department of Chemistry, Princeton University, Washington Road, Princeton, NJ, 08544, USA.
authors.forename: Graham A B
authors.initials: GA
authors.lastname: Hone
authors.affiliation: Department of Chemistry, Emory University, USA.
authors.forename: Damien
authors.initials: D
authors.lastname: Valette
authors.affiliation: Department of Chemistry, The Scripps Research Institute, USA.
authors.forename: Jin-Quan
authors.initials: JQ
authors.lastname: Yu
authors.affiliation: Department of Chemistry, Emory University, USA.
authors.forename: Huw M L
authors.initials: HM
authors.lastname: Davies
authors.affiliation: Frick Chemistry Laboratory, Department of Chemistry, Princeton University, Washington Road, Princeton, NJ, 08544, USA. ejs@princeton.edu.
authors.forename: Erik J
authors.initials: EJ
authors.lastname: Sorensen
keywords: C−H bond activation; natural products; palladation; rhodium carbenes; synthetic methods