Improved process for pilot-scale synthesis of danshensu ((±)-DSS) and its enantiomer derivatives

Organic Process Research and Development

Volumn 18, Issue 12, 2014, Pages 1667-1673

  Bai, Yajun ^a   Zhang, Qunzheng ^b   Jia, Pu ^a   Yang, Lingjian ^a   Sun, Yuhong ^a   Nan, Yefei ^b   Wang, Shixiang ^a   Meng, Xue ^a   Wu, Yizhen ^a   Qin, Fanggang ^a   Sun, Zhe ^a   Gao, Xiaokang ^a   Liu, Pei ^a   Luo, Kai ^a   Zhang, Yajun ^a   Zhao, Xinfeng ^a   Xiao, Chaoni ^a   Liao, Sha ^a   Liu, Jianli ^a   Wang, Cuiling ^a   Fang, Jiacheng ^a   Wang, Xiaoxiao ^a   Wang, Jing ^d   Gao, Rong ^a   An, Xuexia ^a   Zhang, Xunli ^c   Zheng, Xiaohui ^a   more..

^a NORTHWEST UNIVERSITY   (China)

^b XI'AN SHIYOU UNIVERSITY   (China)

^c UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^d Shaanxi Institute of Zoology   (China)

Author keywords

[No Author keywords available]

Indexed keywords

LACTIC ACID; STEREOCHEMISTRY;

CHIRAL HIGH-PERFORMANCE LIQUID CHROMATOGRAPHIES; HIGHER YIELD; IMPROVED PROCESS; INITIAL PROCESS; MEDICINAL CHEMISTRY; PILOT SCALE; PROPANOATE; SCALABLE SYNTHESIS;

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 84919674858     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op4002593     Document Type: Article

References (47)

1. Tang, Y. Q.; Wang, M. H.; Le, X. Y.; Meng, J. N.; Huang, L.; Yu, P.; Chen, J.; Wu, P. Phytomedicine 2011, 18, 1024
2. Liu, M.; Xia, X. H.; Zhang, Z. M.; Wu, Z. J.; Pan, S. Y. J. Chin. Med. Mater. 2009, 32, 265
3. Burdette, J. E.; Chen, S. N.; Lu, Z. Z.; Xu, H. Y.; White, B. E. P.; Fabricant, D. S.; Liu, J.; Fong, H. H. S.; Farnsworth, N. R.; Constantinou, A. I.; Van Breemen, R. B.; Pezzuto, J. M.; Bolton, J. L. J. Agric. Food Chem. 2002, 50, 7022
4. Vergara-Salinas, J. R.; Perez-Jimenez, J.; Torres, J. L.; Agosin, E.; Perez-Correa, J. R. J. Agric. Food Chem. 2012, 60, 10920
5. Negri, G.; Teixeira, E. W.; Alves, M.; Moreti, A.; Otsuk, I. P.; Borguini, R. G.; Salatino, A. J. Agric. Food Chem. 2011, 59, 5516
6. Peng, Z. G.; Chen, H. S. Chin. J. Med. Chem. 2003, 38, 744
7. Dong, C. N.; Wang, Y.; Zhu, Y. Z. Bioorg. Med. Chem. 2009, 17, 3499
8. Wu, L.; Qiao, H.; Li, Y.; Li, L. Phytomedicine 2007, 14, 652
9. Wang, T. F.; Shu, J. J.; Zheng, L. P.; Xiong, L. Y.; Wang, J.; Jin, L.; Wu, Q. Y.; Zou, H.; Zhang, C. Lat. Am. J. Pharm. 2011, 30, 1355
10. De Felice, A.; Bader, A.; Leone, A.; Sosa, S.; Della Loggia, R.; Tubaro, A.; De Tommasi, N. Planta Med. 2006, 72, 643
11. Swarup, V.; Ghosh, J.; Ghosh, S.; Saxena, A.; Basu, A. Antimicrob. Agents Chemother. 2007, 51, 3367
12. Wang, M.; Sun, G. B.; Sun, X.; Wang, H. W.; Meng, X. B.; Qin, M.; Sun, J.; Luo, Y.; Sun, X. B. Toxicol. Lett. 2013, 216, 100
13. Bai, N. S.; He, K.; Roller, M.; Lai, C. S.; Shao, X.; Pan, M. H.; Ho, C. T. J. Agric. Food Chem. 2010, 58, 5363
14. Chlopcikova, S.; Psotova, J.; Miketova, P.; Sousek, J.; Lichnovsky, V.; Simanek, V. Phytother. Res. 2004, 18, 408
15. Osakabe, N.; Yasuda, A.; Natsume, M.; Yoshikawa, T. Carcinogenesis 2004, 25, 549
16. Pei, W. J.; Zhao, X. F.; Zhu, Z. M.; Lin, C. Z.; Zhao, W. M.; Zheng, X. H. J. Chromatogr. B 2004, 809, 237
17. Zheng, X. H.; Zhao, X. F.; Zhao, X.; Wang, S. X.; Wei, Y. M.; Zheng, J. B. J. Sep. Sci. 2007, 30, 851
18. Herbst, R. M.; Shemin, D. Organic Syntheses; Wiley & Sons: New York, 1943; Collect. Vol. No. II, p 1.
19. Buck, J. S.; Ide, W. S. Organic Syntheses; Wiley & Sons: New York, 1943; Collect. Vol. No. II, p 55.
20. Zheng, X. H.; Zhang, Y. C.; Wang, S. X.; Zhao, X. F. Patent Appl. CN 1583710, 2013.
21. Edward, C. B.; Joseph, B. J. Am. Chem. Soc. 1951, 73, 4972
22. Zhang, Q. Z.; Dong, Y.; Nan, Y. F.; Cai, X. D.; Zheng, X. H. Chin. J. Org. Chem. 2009, 29, 1466
23. Reimann, E.; Maas, H. J.; Pflug, T. Monatsh. Chem. 1997, 128, 995
24. Chen, M.; Chen, H.; Wang, Y. Z.; Wang, H. B.; Nan, Y. F.; Zheng, X. H.; Jiang, R. Tetrahedron: Asymmetry 2011, 22, 4
25. Tian, H. L.; Zhou, X. W.; Chen, M.; Wu, J. F.; Zheng, X. H.; Jiang, R. Chin. J. Med. Chem. 2012, 22, 113
26. Wong, H. N. C.; Xu, Z. L.; Chang, H. M.; Lee, C. M. Synthesis 1992, 8, 793
27. Eicher, T.; Ott, M.; Speicher, A. Synthesis 1996, 6, 755
28. Foti, M. C.; Daquino, C.; Geraci, C. J. Org. Chem. 2004, 69, 2309
29. Galland, S.; Mora, N.; Abert-Vian, M.; Rakotomanomana, N.; Dangles, O. J. Agric. Food Chem. 2007, 55, 7573
30. Stevens, R. V.; Beaulieu, N.; Chan, W. H.; Daniewski, A. R.; Takeda, T.; Waldner, A.; Williard, P. G.; Zutter, U. J. Am. Chem. Soc. 1986, 108, 1039
31. Chen, S. N.; Fabricant, D. S.; Pauli, G. F.; Fong, H. H. S.; Farnsworth, N. R. Nat. Prod. Res. 2005, 19, 287
32. Peters, T. A.; Benes, N. E.; Keurentjes, J. T. F. Ind. Eng. Chem. Res. 2005, 44, 9490
33. Xu, Y. J.; Gu, W. Q.; Gin, D. L. J. Am. Chem. Soc. 2004, 126, 1616
34. Astle, M. J.; Schaeffer, B.; Obenland, C. O. J. Am. Chem. Soc. 1955, 77, 3643
35. Li, K. T.; Tsai, L. D.; Wu, C. H.; Wang, I. Ind. Eng. Chem. Res. 2013, 52, 4734
36. Wang, S. B.; Murate, K.; Hayakawa, T. Chem. Commun. 1999, 103
37. Sun, G. B.; Ye, W. P.; Jin, X. L.; Pei, W. W. Chin. J. Struct. Chem. 2003, 22, 747
38. Norbert, B.; Rolf, G.; Markus, K.; Florian, L.; Werner, M. Patent Appl. DE 102006005180, 2006.
39. Hach, V. J. Org. Chem. 1973, 38, 293
40. Dalla, V.; Cotelle, P.; Catteau, J. P. Tetrahedron Lett. 1997, 38, 1577
41. Moilta, H.; Moil, H. U.S. Patent Appl. 5684186, 1997.
42. Faller, J. W.; Lavoie, A. R.; Parr, J. Chem. Rev. 2003, 103, 3345
43. Tokunaga, T.; Okamoto, M.; Tanaka, K.; Tode, C.; Sugiura, M. Anal. Chem. 2010, 82, 4293
44. Wilson, M. L.; Coscia, C. J. J. Org. Chem. 1979, 44, 301
45. Harley-Mason, J. Tetrahedron 1963, 19, 65
46. Chen, H. Z.; Yang, Y. W.; Liu, Y. G.; Wang, R. F.; Ge, J. Y.; Liu, F. Chin. J. Org. Chem. 2005, 25, 1490
47. Billica, H. R.; Adkins, H. Organic Syntheses; Wiley & Sons: New York, 1955; Collect. Vol. No. III, p 176.