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Concise and Practical Asymmetric Synthesis of a Challenging Atropisomeric HIV Integrase Inhibitor
Author(s) -
Fandrick Keith R.,
Li Wenjie,
Zhang Yongda,
Tang Wenjun,
Gao Joe,
Rodriguez Sonia,
Patel Nitinchandra D.,
Reeves Diana C.,
Wu JiangPing,
Sanyal Sanjit,
Gonnella Nina,
Qu Bo,
Haddad Nizar,
Lorenz Jon C.,
Sidhu Kanwar,
Wang June,
Ma Shengli,
Grinberg Nelu,
Lee Heewon,
Tsantrizos Youla,
Poupart MarcAndré,
Busacca Carl A.,
Yee Nathan K.,
Lu Bruce Z.,
Senanayake Chris H.
Publication year - 2015
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.201501575
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.