Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 29, Pages 8270-8274Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201602024
Keywords
C-H bond activation; natural products; palladation; rhodium carbenes; synthetic methods
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Funding
- CCI Center for Selective C-H Functionalization (CCHF) [CHE-1205646]
- Princeton University
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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.
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