1. Concise and Practical Asymmetric Synthesis of a Challenging Atropisomeric HIV Integrase Inhibitor.
- Author
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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, and Tsantrizos, Youla
- Subjects
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HIV integrase inhibitors , *ASYMMETRIC synthesis , *ACYLATION , *LIGANDS (Chemistry) , *SUZUKI reaction - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2015
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