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- Title
Concise and Practical Asymmetric Synthesis of a Challenging Atropisomeric HIV Integrase Inhibitor.
- Authors
Fandrick, Keith R.; Li, Wenjie; Zhang, Yongda; Tang, Wenjun; Gao, Joe; Rodriguez, Sonia; Patel, Nitinchandra D.; Reeves, Diana C.; Wu, Jiang-Ping; Sanyal, Sanjit; Gonnella, Nina; Qu, Bo; Haddad, Nizar; Lorenz, Jon C.; Sidhu, Kanwar; Wang, June; Ma, Shengli; Grinberg, Nelu; Lee, Heewon; Tsantrizos, Youla
- Abstract
A practical and efficient synthesis of a complex chiral atropisomeric HIV integrase inhibitor has been accomplished. The combination of a copper-catalyzed acylation along with the implementation of the BI-DIME ligands for a ligand-controlled Suzuki cross-coupling and an unprecedented bis(trifluoromethane)sulfonamide-catalyzed tert-butylation renders the synthesis of this complex molecule robust, safe, and economical. Furthermore, the overall synthesis was conducted in an asymmetric and diastereoselective fashion with respect to the imbedded atropisomer.
- Subjects
HIV integrase inhibitors; CHEMICAL synthesis; ATROPISOMERS; COPPER; ACYLATION; SUZUKI reaction; FLUOROFORM
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 24, p7144
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201501575