Concise and Practical Asymmetric Synthesis of a Challenging Atropisomeric HIV Integrase Inhibitor. (5th May 2015)

• Record Type: Journal Article
• 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; Poupart, Marc‐André; Busacca, Carl A.; Yee, Nathan K.; Lu, Bruce Z.; Senanayake, Chris H.
• Is Part Of: Angewandte Chemie. Volume 127:Number 24(2015)
• Page Start: 7250
• Page End: 7254
• Publication Date: 2015-05-05
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201501575
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 <italic>tert</italic>‐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.</p> </abstract>