Premium
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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201602024
Subject(s) - carbene , chemistry , combinatorial chemistry , tricyclic , core (optical fiber) , surface modification , stereochemistry , organic chemistry , computer science , catalysis , telecommunications
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.