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Rapid Construction of a Benzo‐Fused Indoxamycin Core Enabled by Site‐Selective C−H Functionalizations
Author(s) -
Bedell T. Aaron,
Hone Graham A. B.,
Valette Damien,
Yu JinQuan,
Davies Huw M. L.,
Sorensen Erik J.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201602024
Subject(s) - chemistry , carbene , combinatorial chemistry , surface modification , tricyclic , core (optical fiber) , stereochemistry , nanotechnology , organic chemistry , catalysis , materials science , composite material
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.