Progresses in total synthesis of englerin A and biological evaluations of its analogues

Chinese Journal of Organic Chemistry

Volumn 32, Issue 1, 2012, Pages 1-12

  Lu, Yunyu ^a,b   Yao, Hequan ^a   Sun, Bingfeng ^b  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Biological evaluation; Englerin A; Progress; Total synthesis

Indexed keywords

EID: 84860187174     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: 10.6023/cjoc1110141     Document Type: Review

References (55)

1. Rini, B I.; Campbell, S. C. Lancet 2009, 373, 1119.
2. Atkins, B. A.; Ernstoff, M. S.; Figlin, R. A.; Flaherty, K. T.; George, D. J.; Kaelin, W. G.; Kwon, E.D.; Libermann, T. A.; Linehan, W. M.; McDermott, D. F.; Ochoa, A. C.; Pantuck, A. J.; Rini, B. I.; Rosen, M. A.; Sosraan, J. A.; Sukhatme, V. P.; Vieweg, J. W.; Wood, C. G.; King, L. Clin. Cancer Res. 2007, 13(suppl. 2), 667s.
3. Furge, K. A.; MacKeigan, J. P.; Teh, B. T. Lancet Oncol. 2010, 11, 571.
4. Newman, D. J.; Cragg, G.M.J. Nat. Prod. 2007, 70, 461.
5. (a) Newman, D. J. J. Med. Chem. 2008, 51, 2589.
6. (b) Cragg, G. M.; Newman, D. J. Chem. Rev. 2009, 7, 3012.
7. Cragg, G. M.; Newman, D. J. Phytochem. Rev. 2009, 8, 313.
8. (a) Ratnayake, R.; Covell, D.; Ransom, T. T.; Gustafson, K. R.; Beutler, J. A. Org. Lett. 2008, 11, 57.
9. (b) Beutler, J. A.; Ratnayake, R.; Covell, D.; Johnson, T. R. WO 2009/088854, 2009
10. [Chem. Abstr. 2009, 151, 148487].
11. http://dtp.nci.nih.gov/dtpstandard/cancerscreeningdata/index.jsp.
12. (a) Willot, M.; Radtke, L.; Konning, D.; Frohlich, R.; Gess-ner, V. H.; Strohmann, C.; Christmann, M. Angew. Chem., Int. Ed. 2009, 45, 9105.
13. (b) Zhou, Q.; Chen, X.; Ma, D. Angew. Chem., Int. Ed. 2010, 49, 3513.
14. (c) Molawi, K.; Delpont, N.; Echavarren, A. M. Angew. Chem., Int. Ed. 2010, 49, 3517.
15. (d) Nicolaou, K. C.; Kang, Q.; Ng, S. Y.; Chen, D. Y.-K. J. Am. Chem. Soc. 2010, 132, 8219.
16. (e) Xu, J.; Caro-Diaz, E. J. E.; Theodorakis, E. A. Org. Lett. 2010, 12, 3708.
17. (f) Sun, B.-F.; Wang, C.-L.; Ding, R.; Xu, J.-Y.; Lin, G.-Q. Tetrahedron Lett. 2011, 52, 2155.
18. (g) Chan, K. P.; Chen, D. Y.-K. Chem Med Chem 2011, 6, 420.
19. (h) Navickas, V.; Ushakov, D. B.; Maier, M. E.; Strobele, M.; Meyer, H. J. Org. Lett. 2010, 12, 3418.
20. (i) Ushakov, D. B.; Navickas, V.; Ströbele, M.; Maichle- Mössmer, C; Sasse, F.; Maier, M. E. Org. Lett. 2011, 75, 2090.
21. (O) Radtke, L.; Willot, M.; Sun, H.; Ziegler, S.; Sauerland, S.; Strohmann, C.; Frohlich, R.; Habenberger, P.; Waldmann, H.; Christmann, M. Angew. Chem., Int. Ed. 2011, 50, 3998.
22. (k) Li, Z.; Nakashige, M.; Chain, W. J. J. Am. Chem. Soc. 2011, 133, 6553.
23. (a) Connolly, J. D.; Hill, R. A. Dictionary of Terpenoids, Vol. 1, Chapman & Hall, London, 1991, p. 476.
24. (b) Fraga, B. M. Nat. Prod. Rep. 2011, 28, 1580.
25. (a) Zhuzbaev, B. T.; Adekenov, S. M.; Veselovskii, V. V. Russ. Chem. Rev. 1995, 64, 187.
26. (b) Hanson, J. R. In The Total Synthesis of Natural Products, Vol. 11, Eds.: Pirrung, M. C.; Morehead, A. T.; Young, B. G., Wiley-lnterscience, New York, 1999, p. 732.
27. (c) Schall, A.; Reiser, O. Eur. J. Org. Chem. 2008, 14, 2353.
28. (d) Foley, D. A.; Maguire, A. R. Tetrahedron 2010, 66, 1131.
29. (a) Orientalol, E.; Orientalol, F.; Peng, G. P.; Tian, G.; Huang, X. F.; Lou, F. C. Photochemistry 2003, 63, 877.
30. (b) Pubinemoid, B.; Huang, S. X.; Yang, J.; Xiao, W. L.; Zhu, Y. L.; Li, R. T.; Li, L. M.; Pu, J. X.; Li, X.; Li, S. H.; Sun, H. D. Helv. Chim. Acta 2006, 89, 1169.
31. (c) For 7: Sutthivaiyakit, S.; Nakorn, N. N.; Kraus, W.; Sutthivaiyakit, P. Tetrahedron 2003, 59, 9991.
32. (d) For 8: Stierle, A. A.; Stierle, D. B.; Goldstein, E.; Parker, K.; Bugni, T.; Baarson, C.; Gress, J.; Blake, D. J. Nat. Prod. 2003, 66, 1097.
33. (e) For 9: Wang, H. X.; Liu, C. M.; Liu, Q.; Gao, K. Phytochemistry 2008, 69, 2088.
34. Maimone, T. J.; Baran, P. S. Nat. Chem. Biol. 2007, 3, 396.
35. (a) Cane, D. E. In Comprehensive Natural Product Chemistry, Vol. 2, Eds.: Barton, D.; Nakanishi, K.; Meth-Cohn, O., Elsevier, Amsterdam, 1999, p. 155.
36. (b) Drew, D. P.; Krichau, N.; Reichwald, K.; Simonsen, H. T. Phytochem. Rev. 2009, 8, 581.
37. (c) Chappell, J.; Coates, R. M. In Comprehensive Natural Products II, Vol. 9, Eds.: Mander, L.; Liu H.-W., Elsevier, Amsterdam, 2010, p. 609.
38. Asakawa, Y.; Noma, Y. In Comprehensive Natural Products II, Vol. 3, Eds.: Mander, L.; Liu H.-W., Elsevier, Amsterdam, 2010, p. 803.
39. Jomemez-Nunez, E.; Claverie, C. K.; Nieto-Oberhuber, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 118, 5578.
40. Willot, M.; Christmann, M. Nat. Chem. 2010, 2, 519.
41. Jimenez-Nunez, E.; Molawi, K.; Echavarren, A. M. Chem. Commun. 2009, 47, 7321.
42. Jeong, N.; Robinson, J. E.; Wender, P. A.; Gamber, G. G.; Williams, T. J.; Davies, H. M. L.; Walji, A. M. In Modem Rhodium-Catalyzed Organic Reactions, Ed.: Evans, P. A., Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2005, Chapters 11.14, p.215.
43. (a) Nicolaou, K. C.; Ellery, S. P.; Chen, J. S. Angew. Chem., Int. Ed. 2009, 48, 7140.
44. (b) Szostak, M.; Procter, D. J. Angew. Chem., Int. Ed. 2011, 50, 7737.
45. (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
46. (b) Padwa, A. Helv. Chim. Acta 2005, 88, 1357.
47. (c) Singh, V.; Murali Krishna, U.; Vikrant; Trivedi, G. K. Tetrahedron 2008, 64, 3405.
48. (d) Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577.
49. (e) Muthusamy, S.; Krishnamurthi, J. Top. Heterocycl. Chem. 2008, 12, 147.
50. Navickas, V. PhD. Dissertation, University of Tubingen, Tubingen, 2011.
51. Harmata, M.; Ghosh, S. K.; Hong, X.; Wacharasindhu, S.; Kirchhoefer, P. J. Am. Chem. Soc. 2003, 125, 2058.
52. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
53. Knauseder, F.; Brandl, E. J. Antibiot. 1976, 29, 125.
54. Saito, N.; Kameyama, N.; Kubo, A. Tetrahedron 2000, 56, 9937.
55. Costantino, V.; Dell'Aversano, C.; Fattorsusso, E.; Mangno, A. Steroids 2000, 65, 138.