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- Title
Rapid Construction of a Benzo-Fused Indoxamycin Core Enabled by Site-Selective C--H Functionalizations.
- Authors
Bedell, T. Aaron; Hone, Graham A. B.; Valette, Damien; Yu, Jin ‐ Quan; Davies, Huw M. L.; Sorensen, Erik J.
- 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.
- Subjects
CARBON-hydrogen bonds; METABOLITES; RING formation (Chemistry); CHEMICAL synthesis; INSERTION reactions (Chemistry); CARBENES
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 29, p8410
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201602024