Scalable Synthesis of the Potent HIV Inhibitor BMS-986001 by Non-enzymatic Dynamic Kinetic Asymmetric Transformation (DYKAT)

Angewandte Chemie - International Edition

Volumn 54, Issue 24, 2015, Pages 7185-7188

  Ortiz, Adrian ^a   Benkovics, Tamas ^a   Beutner, Gregory L ^a   Shi, Zhongping ^a   Bultman, Michael ^a   Nye, Jeffrey ^a   Sfouggatakis, Chris ^a   Kronenthal, David R ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

inhibitors; kinetic resolution; organocatalysis; synthesis design; tautomerism

Indexed keywords

CHROMATOGRAPHY; CORROSION INHIBITORS; KINETICS; MOLECULES;

CHROMATOGRAPHY-FREE SYNTHESIS; DYNAMIC KINETIC ASYMMETRIC TRANSFORMATIONS; DYNAMIC KINETIC RESOLUTION; KINETIC RESOLUTION; ORGANOCATALYSIS; ORGANOCATALYTIC TRANSFORMATION; SYNTHESIS DESIGN; TAUTOMERISM;

SYNTHESIS (CHEMICAL);

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; BMS-986001; LEVAMISOLE; THYMIDINE;

ANALOGS AND DERIVATIVES; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTI-HIV AGENTS; CATALYSIS; LEVAMISOLE; STEREOISOMERISM; THYMIDINE;

EID: 84930682144     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201502290     Document Type: Article

References (29)

1. For a recent review, see:, S. Broder, Antiviral Res. 2010, 85, 1-18.
2. E. L. Asahchop, M. A. Wainberg, R. D. Sloan, C. L. Tremblay, Antimicrob. Agents Chemother. 2012, 56, 5000-5008, and references therein.
3. Panel on Antiretroviral Guidelines for Adults and Adolescents. Guidelines for the Use of Antiretroviral Agents in HIV-1-infected Adults and Adolescents: 2012 Update. Washington, DC: U.S. Department of Health and Human Services, 2012.
4. L. Cotte, P. Dellamonica, F. Raffi, Y. Yazdanpanah, J.-M. Michela Molina, F. Boué, Y. Urata, H. P. Chan, L. Zhu, I. Chang, R. Bertz, G. J. Hanna, D. M. Grasela, C. Hwang, J. Acquired Immune Defic. Syndr. 2013, 63, 346-354
5. F. Wang, O. P. Flint, Antimicrob. Agents Chemother. 2013, 57, 6205-6212
6. G. Yang, G. E. Dutschman, C. J. Wang, H. Tanaka, M. Baba, K. S. Anderson, Y. C. Cheng, Antiviral Res. 2007, 73, 185-191
7. G. E. Dutschman, S. P. Grill, E. A. Gullen, K. Haraguchi, S. Takeda, H. Tanaka, M. Baba, Y. C. Cheng, Antimicrob. Agents Chemother. 2004, 48, 1640-1646.
8. H. Takayama, Z. Jia, L. Kremer, J. O. Bauer, C. Strohmann, S. Ziegler, A. P. Antonchock, H. Waldman, Angew. Chem. Int. Ed. 2013, 52, 12404-12408
9. Angew. Chem. 2013, 125, 12630-12634
10. M. A. Ali, N. Bhogal, J. B. C. Findlay, C. W. G. Fishwick, J. Med. Chem. 2005, 48, 5655-5658
11. K. L. Jackson, J. A. Henderson, J. C. Morris, H. Motoyoshi, A. J. Phillips, Tetrahedron Lett. 2008, 49, 2939-2941
12. K. C. Nicolaou, M. O. Fredrick, A. C. B. Burtuloso, R. M. Denton, F. Rivas, K. P. Cole, R. J. Aversa, R. Gibe, T. Umezawa, T. Suzuki, J. Am. Chem. Soc. 2008, 130, 7466-7476
13. R. Jones, M. J. Kriche, Org. Lett. 2009, 11, 1849-1851.
14. N. Z. Burns, M. R. Whitten, E. N. Jacobsen, J. Am. Chem. Soc. 2011, 133, 14578-14581
15. T. C. Coombs, M. D. Lee, H. Wong, M. Armstrong, B. Cheng, W. Chen, A. F. Moretto, L. S. Liebeskind, J. Org. Chem. 2008, 73, 882-888
16. A. Orue, E. Reyes, J. L. Vicario, L. Carillo, U. Uria, Org. Lett. 2012, 14, 3740-3743.
17. M. P. Georgiadis, K. E. Albizati, T. M. Georgiadis, Org. Prep. Proced. 1992, 24, 95-118.
18. T. Benkovics, A. Ortiz, Z. Guo, A. Goswami, P. Deshpande, Org. Synth. 2014, 91, 293-306.
19. M. Van den Heuvel, A. D. Cuiper, H. Van der Deen, R. M. Kellogg, B. L. Feringa, Tetrahedron Lett. 1997, 38, 1655-1658.
20. A. Yamazaki, Y. Iriyama, Y. Ootsuka, H. Kurihara, (Nissan Chemical Industries), WO201126082, 2011.
21. G. C. Fu, Acc. Chem. Res. 2004, 37, 542-547.
22. X. Li, V. Birman, Org. Lett. 2006, 8, 1351-1354.
23. For a review see:, P. R. Jones, Chem. Rev. 1963, 63, 461-487
24. L. Guasch, M. Sitzmann, M. C. Nicklaus, J. Chem. Inf. Model. 2014, 54, 2423-2432
25. Y. C. Martin, J. Comput.-Aided Mol. Des. 2009, 23, 693-704.
26. Advances in Carbohydrate Chemistry and Biochemistry, Vol. 24 (Eds.:, M. L. Wolfrom, R. S. Tipson,), Academic Press, New York, 1969, pp. 43-63.
27. L. J. Wilson, D. Liotta, Tetrahedron Lett. 1990, 31, 1815-1818.
28. A. L. Marzinzik, K. B. Sharpless, J. Org. Chem. 2001, 66, 594-596.
29. "Sulfilimine and Sulfoxide Methods for the Preparation of Festinavir":, A. Ortiz, T. Benkovics, Z. Shi, P. P. Deshpande, Z. Guo, D. R. Kronenthal, C. Sfouggatakis, WO2013177243A1, 2013.