Angewandte Chemie - International Edition p. 7144 - 7148 (2015)
Update date:2022-08-05
Topics:
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.
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. Atropselective: An efficient asymmetric synthesis of an atropisomeric HIV inhibitor has been accomplished. The combination of a copper-catalyzed acylation with the implementation of 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.
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Doi:10.1021/acsmedchemlett.8b00094
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