Total synthesis of entecavir

Journal of Organic Chemistry

Volumn 78, Issue 11, 2013, Pages 5482-5491

  Velasco, Javier ^a,b   Ariza, Xavier ^a,c   Badía, Laura ^b   Bartra, Martí ^b   Berenguer, Ramon ^b   Farràs, Jaume ^a   Gallardo, Joan ^a   Garcia, Jordi ^a,c   Gasanz, Yolanda ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b Department of Research and Development   (Spain)

^c Instituto de Salud Carlos III   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CONDENSATION REACTIONS; KETONES;

BORON ALDOL REACTIONS; CARBON SKELETON; KEY FEATURE; MITSUNOBU REACTIONS; PURINE DERIVATIVES; RADICAL ADDITION; STEREO-SELECTIVE; TOTAL SYNTHESIS;

CYCLIZATION;

6 CHLOROPURINE; ACROLEIN; ALKYNE; BORON; CARBON; CYCLOPENTANE; ENTECAVIR; EPOXIDE; FORMIC ACID; METHYLENECYCLOPENTANE; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; CRYSTALLIZATION; CYCLIZATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HYDROLYSIS; MITSUNOBU REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 84879298192     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400607v     Document Type: Article

References (56)

1. Hepatitis B; Fact sheet No. 204; World Health Organization, July 2012. http://www.who.int/mediacentre/factsheets/fs204/en/index.html (accessed March 22, 2013).
2. Dienstag, J. L. N. Engl. J. Med. 2008, 359, 1486-1500
3. Scott, L. J.; Keating, G. M. Drugs 2009, 69, 1003-1033
4. Zahler, R.; Slusarchyk, W. A. Eur. Pat. EP0481754 B1, August 20, 1997.
5. Bisacchi, G. S.; Sundeen, J. E. WO9809964 A1, August 26, 1997.
6. Bisacchi, G. S.; Chao, S. T.; Bachard, C.; Daris, J. P.; Innaimo, S.; Jacobs, G. A.; Kocy, O.; Lapointe, P.; Martel, A.; Merchant, Z.; Slusarchyk, W. A.; Sundeen, J. E.; Young, M. G.; Colonno, R.; Zahler, R. Bioorg. Med. Chem. Lett. 1997, 7, 127-132
7. Innaimo, S. F.; Seifer, M.; Bisacchi, G. S.; Standring, D. N.; Zahler, R.; Colonno, R. J. Antimicrob. Agents Chemother. 1997, 41, 1444-1448
8. Gu, Y.; Cai, R.; Sun, X.; Zhu, H.; Zhao, Y. (Suzhou Well-Bridge Biological Technology Co., Ltd., Peop. Rep. China) CN102924454, A, February 13, 2013.
9. Jung, I. H.; Jang, M. S.; Kim, G. N. (Sungwun Pharmacopia Co., Ltd., S. Korea; Hanseo Chemical Co., Ltd.) KR2012091971, A, August 20, 2012.
10. Chen, H.; Jin, Y. (Shanghai Yonghong Industry Group Chemical Technology Co., Ltd., Peop. Rep. China) CN102477036, A, May 30, 2012.
11. Zheng, Z. (Ausun Pharmatech Co. Ltd., Peop. Rep. China) WO2012006964, A1, January 19, 2012.
12. Alberico, D.; Gorin, B.; Beharrilall, R.; Dixon, C.; Clayton, J.; Rexon, V. WO2011150513, A1, December 8, 2011.
13. Xu, K.; Wang, J.; Zhong, D.; Li, Z.; Hao, J. (Hainan Weikang Pharmaceutical (Qianshan) Co., Ltd., Peop. Rep. China) CN102225938, A, October 26, 2011.
14. Hu, T.-C.; Huang, H.-T. (Scinopharm Taiwan Ltd.) US2011201809, A1, August 18, 2011.
15. Li, G.; Qiu, B.; Yang, X.; Chen, S. (Fujian Cosunter Pharmaceutical Co., Ltd., Peop. Rep. China) CN102491960, A, Jun 13, 2012.
16. Lee, J. H.; Park, G. S.; Kim, J. H.; Choi, T. J.; Lee, J. E.; Han, J. H.; Bang, H. J.; Jung, S. Y.; Chang, Y. K.; Lee, G. S.; Kim, M. S. (Hanmi Holdings Co., Ltd., S. Korea) WO2011046303, A2, April 21 2011.
17. Lee, J.; Park, G.-S.; Kim, J. H.; Lee, J. E.; Park, C. H.; Choi, T. J.; Park, E.-J.; Kim, C. K.; Lim, E. J.; Chang, Y.-K.; Lee, G. S. (Hanmi Pharm. Ind. Co., Ltd., S. Korea) WO2010074534, A2, July 1, 2010.
18. Fang, Y.; Li, C.; Yin, F. (Hande Pharma Ltd., Peop. Rep. China) CN101891741, A, November 24, 2010.
19. Lei, X.; Lin, G.; Zeng, Y. (Fudan University, Peop. Rep. China) CN101781301, A, July 21, 2010.
20. Zhou, Z.; Wei, X.; Xu, X.; Chen, H. (Shanghai Pharmaceutical Co., Ltd., Peop. Rep. China) CN101759698, A, June 30, 2010.
21. Zeng, Y.; Wang, Z.; Gao, D.; Xu, Z. (Anhui Biochem. United Pharmaceutical Co., Ltd., Peop. Rep. China) CN101531660, A, September 16, 2009.
22. Liu, K.; Li, Y.; Wang, H.; Gao, X.; Tao, X.; Zhao, P.; Luo, G.; Tan, Y.; Yin, H.; Zhang, J. (Leadingpharm Laboratories Inc., Peop. Rep. China) CN 101337962, A, January 07, 2009.
23. Zhao, J.; Li, X.; Zhu, J.; Lou, J.; Zhou, X.; Cai, X.; Dong, Y.; Ye, X.; Zhang, M.; Xu, Z.; Wei, W.; Liu, W. (Hangzhou Shengyou Pharmaceutical Technology Co., Ltd., Peop. Rep. China; Tianjin Taipu Medicine Science and Technology Development Co., Ltd.; Shanghai Guochuang Pharmaceutical Co., Ltd.) CN101210015, A, July 02, 2008.
24. Kang, H. Fujian Guangshengtang Pharmaceutical Co., Ltd., Peop. Rep. China) CN101182322, A, May 21, 2008.
25. Yan, H. CN101148450, A, March 26, 2008.
26. Yuan, J.; Zhang, X.; Liu, F.; Zhang, K.; Ye, X.; Ge, Y. (Jiangsu Chia-Tai Tianqing Pharmaceutical Co., Ltd., Peop. Rep. China; Brightgene Bio-Medical Tech Ltd.) CN101130542, A, February 27, 2008.
27. Jiang, W.; Wang, W.; Hu, Y. (SFFT Developing Co., Ltd., Peop. Rep. China) CN101050216, A, October 10, 2007.
28. Chen, Y.; Han, S.; Yin, J.; Sun, T.; Cai, W.; Zhang, Y.; Ruan, G.; Zhu, Q.; Wang, X. (Shanghai Yangfan Pharmaceutical Technology Co., Ltd., Peop. Rep. China; Jiangsu Yangtze River Pharmaceutical Group) CN101012228, A, August 08, 2007.
29. Zhang, L.; Zeng, Z.; Yang, L.; Guo, L. (Shanghai Zhongxia Chemical Co., Ltd., Peop. Rep. China) CN1861602, A, November 15, 2006.
30. Zhou, M. X.; Reiff, E. A.; Vemishetti, P.; Pendri, Y. R.; Singh, A. K.; Prasad, S. J.; Dhokte, U. P.; Qian, X.; Mountford, P.; Hartung, K. B.; Sailes, H. (Bristol-Myers Squibb Company, USA), WO2005118585, A1, December 15, 2005.
31. Pendri, Y. R.; Chen, C. H.; Patel, S. S.; Evans, J. M.; Liang, J.; Kronenthal, D. R.; Powers, G. L.; Prasad, S. J.; Bien, J. T.; Shi, Z.; Patel, R. N.; Chan, Y. Y.; Rijhwani, S. K.; Singh, A. K.; Wang, S.; Stojanovic, M.; Polniaszek, R.; Lewis, C.; Thottathil, J.; Krishnamurty, D.; Zhou, M. X.; Vemishetti, P. (Bristol-Myers Squibb Company, USA), WO2004052310, A3, December 10, 2003.
32. Guo, L. W.; Xiao, Y. J.; Yang, L. P. Chin. Chem. Lett. 2006, 17, 907-910
33. Ying, L.; Wang, Z. (Shanghai Changsen Pharmaceutical Co., Ltd., Peop. Rep. China) CN102863444, A, January 9, 2013.
34. Fan, M.; Mao, J.; Si, B.; Feng, J. (Shanghai Changsen Pharmaceutical Co., Ltd., Peop. Rep. China) CN102417506, A, April 18, 2012.
35. Liu, X.; Jiao, X.; Wu, Q.; Tian, C.; Li, R.; Xie, P. Tetrahedron Lett. 2012, 53, 3805-3807
36. Zhou, B.; Li, Y. Tetrahedron Lett. 2012, 53, 502-504
37. Rawal, R. K.; Singh, U. S.; Gadthula, S.; Chu, C. K. Curr. Protoc. Nucleic Acid Chem. 2011, 47, 14.7.1-14.7.17
38. Bartra, M.; Berenguer, R.; Velasco, J.; Ariza, J.; Farràs, J.; García, J. (Esteve Química, S.A., Spain) WO2012085209, A1, June 28, 2012.
39. Berenguer, R.; Badia, L.; Gasanz, Y.; Velasco, J.; Ariza, X. (Esteve Química, S.A., Spain) PCT/EP2012/073438, November 24, 2011.
40. Boutureira, O.; Matheu, M. I.; Díaz, Y.; Castillón, S. Chem. Soc. Rev. 2013, 10.1039/C3CS00003F
41. Matyugina, E. S.; Khandazhinskaya, A. L.; Kochetkov, S. N. Russ. Chem. Rev. 2012, 81, 729-746
42. Wang, J.; Rawal, R. K.; Chu, C. K. Recent Advances in Carbocyclic Nucleosides: Synthesis and Biological Activity. In Medicinal Chemistry of Nucleic Acids; Zhang, L.-H.; Xi, Z.; Chattopadhyaya, J., Eds.; Wiley & Sons: Hoboken, NJ, 2011; pp 1-100.
43. Nugent, W. A.; RajanBabu, T. V. J. Am. Chem. Soc. 1988, 110, 8561-8562
44. RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986-997
45. Rossi, B.; Prosperini, S.; Pastori, N.; Clerici, A.; Punta, C. Molecules 2012, 17, 14700-14732
46. Cuerva, J. M.; Justicia, J.; Oller-López, J. L.; Bazdi, B.; Oltra, J. E. Mini-Rev. Org. Chem. 2006, 3, 23-35
47. Cuerva, J. M.; Justicia, J.; Oller-López, J. L.; Oltra, J. E. Top. Curr. Chem. 2006, 264, 63-91
48. Barrero, A. F.; Quílez del Moral, J. F.; Sánchez, E. M.; Arteaga, J. F. Eur. J. Org. Chem. 2006, 1627-1641
49. Ziegler, F. E.; Sarpong, M. A. Tetrahedron 2003, 59, 9013-9018
50. For a recent review, see: Ariza, X.; Garcia, J.; Romea, P.; Urpí, F. Synthesis 2011, 2175-2191
51. Paterson, I.; Goodman, J. M.; Lister, M. A.; Schumann, R. C.; McClure, C. K.; Norcross, R. D. Tetrahedron 1990, 46, 4663-4684
52. Paterson, I.; Perkins, M. V. Tetrahedron 1996, 52, 1811-1834 and references therein
53. Gansäuer, A.; Pierobon, M.; Bluhm, H. Angew. Chem., Int. Ed. 1998, 37, 101-103
54. Andreas Gansäuer, A.; Bluhm, H.; Pierobon, M. J. Am. Chem. Soc. 1998, 120, 12849-12859
55. Barrero, A. F.; Rosales, A.; Cuerva, J. M.; Oltra, J. E. Org. Lett. 2003, 5, 1935-1938
56. Gansäuer, A.; Otte, M.; Shi, L. J. Am. Chem. Soc. 2011, 133, 416-417