Literature DB >> 25939331

Concise and Practical Asymmetric Synthesis of a Challenging Atropisomeric HIV Integrase Inhibitor.

Keith R Fandrick1, Wenjie Li2, Yongda Zhang2, Wenjun Tang2, Joe Gao2, Sonia Rodriguez2, Nitinchandra D Patel2, Diana C Reeves2, Jiang-Ping Wu2, Sanjit Sanyal2, Nina Gonnella2, Bo Qu2, Nizar Haddad2, Jon C Lorenz2, Kanwar Sidhu2, June Wang2, Shengli Ma2, Nelu Grinberg2, Heewon Lee2, Youla Tsantrizos3, Marc-André Poupart3, Carl A Busacca2, Nathan K Yee2, Bruce Z Lu2, Chris H Senanayake2.   

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.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Suzuki couplings; acylation; asymmetric synthesis; phosphine ligands; tert-butylation

Mesh：

Substances：

Year:  2015        PMID： 25939331     DOI： 10.1002/anie.201501575

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  6 in total

Review 1.  Atropisomerism in medicinal chemistry: challenges and opportunities.

Authors:  Sean T Toenjes; Jeffrey L Gustafson
Journal:  Future Med Chem       Date:  2018-01-30       Impact factor: 3.808

2.  Enantioselective Synthesis of Pyrrolopyrimidine Scaffolds through Cation-Directed Nucleophilic Aromatic Substitution.

Authors:  Mariel M Cardenas; Sean T Toenjes; Christopher J Nalbandian; Jeffrey L Gustafson
Journal:  Org Lett       Date:  2018-03-21       Impact factor: 6.005

3.  An Isoquinoline Scaffold as a Novel Class of Allosteric HIV-1 Integrase Inhibitors.

Authors:  Tyler A Wilson; Pratibha C Koneru; Stephanie V Rebensburg; Jared J Lindenberger; Matthew J Kobe; Nicholas T Cockroft; Daniel Adu-Ampratwum; Ross C Larue; Mamuka Kvaratskhelia; James R Fuchs
Journal:  ACS Med Chem Lett       Date:  2019-01-30       Impact factor: 4.345

4.  Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-ortho-Substituted Biaryl Synthesis.

Authors:  Nitinchandra Dahyabhai Patel; Joshua D Sieber; Sergei Tcyrulnikov; Bryan J Simmons; Daniel Rivalti; Krishnaja Duvvuri; Yongda Zhang; Donghong A Gao; Keith R Fandrick; Nizar Haddad; Kendricks So Lao; Hari Prasad Reddy Mangunuru; Soumik Biswas; Bo Qu; Nelu Grinberg; Scott Pennino; Heewon Lee; Jinhua J Song; B Frank Gupton; Neil K Garg; Marisa C Kozlowski; Chris H Senanayake
Journal:  ACS Catal       Date:  2018-09-20       Impact factor: 13.084

5.  Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: preparation of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate and derivatives.

Authors:  Nicholas G Jentsch; Jared D Hume; Emily B Crull; Samer M Beauti; Amy H Pham; Julie A Pigza; Jacques J Kessl; Matthew G Donahue
Journal:  Beilstein J Org Chem       Date:  2018-09-28       Impact factor: 2.544

6.  Indole-based allosteric inhibitors of HIV-1 integrase.

Authors:  Pratiq A Patel; Nina Kvaratskhelia; Yara Mansour; Janet Antwi; Lei Feng; Pratibha Koneru; Mathew J Kobe; Nivedita Jena; Guqin Shi; Mosaad S Mohamed; Chenglong Li; Jacques J Kessl; James R Fuchs
Journal:  Bioorg Med Chem Lett       Date:  2016-08-13       Impact factor: 2.823
  6 in total

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