Asymmetric synthesis of (R)-antofine and (R)-cryptopleurine via proline-catalyzed sequential α-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehyde

Journal of Organic Chemistry

Volumn 75, Issue 20, 2010, Pages 7018-7021

  Cui, Mingbo ^a   Song, Hongjian ^a   Feng, Anzheng ^a   Wang, Ziwen ^a   Wang, Qingmin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; ENANTIOPURE; NATURALLY OCCURRING; OPTICAL PURITY; WADSWORTH-EMMONS OLEFINATION;

ALDEHYDES; CATALYSIS; ISOMERS; METABOLITES; NITROGEN COMPOUNDS;

AMINO ACIDS;

ALDEHYDE; ANTOFINE; CRYTOPLEURINE; INDOLIZIDINE ALKALOID; PROLINE; UNCLASSIFIED DRUG;

ALPHA AMINOXYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; HORNER WADSWORTH EMMONS REACTION; ISOMER; OLEFINATION; OPTICS;

ALDEHYDES; ALKALOIDS; CATALYSIS; INDOLES; MOLECULAR STRUCTURE; PHENANTHROLINES; PROLINE; STEREOISOMERISM;

EID: 77957924308     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101510x     Document Type: Article

References (63)

1. Reviews: Li, Z.; Jin, Z.; Huang, R. Synthesis 2001, 2365-2378
2. Gellert, E. J. Nat. Prod. 1982, 45, 50-73
3. Bick, I. R. C.; Sinchai, W. The Alkaloids 1981, 19, 193-220
4. Govindachari, T. R.; Viswanathan, N. Heterocycles 1978, 11, 587-613
5. Chemler, S. R. Curr. Bioact. Compd. 2009, 5, 2-19
6. Strk, D.; Lykkeberg, A. K.; Christensen, J. B.; Budnik, A.; Abe, F.; Jaroszewski, J. W. J. Nat. Prod. 2002, 65, 1299-1302
7. Luo, Y.; Liu, Y.; Luo, D.; Gao, X.; Li, B.; Zhang, G. PlantaMed. 2003, 69, 842-845
8. Banwell, M. G.; Bezos, A.; Burns, C.; Kruszeknicki, I.; Parish, C. R.; Su, S.; Sydnes, M. O. Bioorg. Med. Chem. Lett. 2006, 16, 181-185
9. Chuang, T. H.; Lee, S. J.; Yang, C. W.; Wu, P. L. Org. Biomol. Chem. 2006, 4, 860-867
10. Fu, Y.; Lee, S. K.; Min, H. Y.; Lee, T.; Lee, J.; Cheng, M.; Kim, S. Bioorg. Med. Chem. Lett. 2007, 17, 97-100
11. Yang, C. W.; Chuang, T. H.; Wu, P. L.; Huang, W. H.; Lee, S. J. Biochem. Biophys. Res. Commun. 2007, 354, 942-948
12. Gao, W.; Busson, S.; Grill, S. P.; Gullen, E. A.; Hu, Y. C.; Huang, X.; Zhong, S.; Kaczmarek, C.; Gutierrez, J.; Francis, S.; Baker, D. C.; Yu, S.; Cheng, Y. C. Bioorg. Med. Chem. Lett. 2007, 17, 4338-4342
13. Gao, W. L.; Chen, A. P. C.; Leung, C. H.; Gullen, E. A.; Fürstner, A.; Shi, Q.; Wei, L.; Lee, K. H.; Cheng, Y. C. Bioorg. Med. Chem. Lett. 2008, 18, 704-709
14. Yang, X.; Shi, Q.; Bastow, K. F.; Lee, K. H. Org. Lett. 2010, 12 (7) 1416-1419
15. Suffness, M.; Douros, J. In Anticancer Agents Based on Natural Product Models; Cassady, J. M.; Douros, J. D., Eds.; Academic Press: London, 1980; Med. Chem. Vol. 16, pp 465 - 487.
16. The 60 cell line NCI test data, along with in vivo data, can be accessed from the NSC numbers: http://dtp.nci.nih.gov/dtpstandard/dwindex/index.jsp.
17. Gao, W.; Lam, W.; Zhong, S.; Kaczmarek, C.; Baker, D. C.; Cheng, Y. C. Cancer Res. 2004, 64, 678-688
18. For the most recent examples, see: Kim, S.; Lee, J.; Lee, T.; Park, H. G.; Kim, D. Org. Lett. 2003, 5, 2703-2706
19. Kim, S.; Lee, T.; Lee, E.; Lee, J.; Fan, G. J.; Lee, S. K.; Kim, D. J. Org. Chem. 2004, 69, 3144-3149
20. Furstner, A.; Kennedy, J. W. Chem. Eur. J. 2006, 12, 7398-7410
21. Kim, S.; Lee, Y. M.; Lee, J.; Lee, T.; Fu, Y.; Song, Y.; Cho, J.; Kim, D. J. Org. Chem. 2007, 72, 4886-4891
22. Zeng, W.; Chemler, S. R. J. Org. Chem. 2008, 73, 6045-6047
23. McIver, A.; Young, D. D.; Deiters, A. Chem. Commun. 2008, 39, 4750-4752
24. Yamashita, S.; Kurono, N.; Senboku, H.; Tokuda, M.; Orito, K. Eur. J. Org. Chem. 2009, 1173-1180
25. Rossiter, L. M.; Slater, M. L.; Giessert, R. E.; Sakwa, S. A.; Herr, R. J. J. Org. Chem. 2009, 74, 9554-9557
26. Stoye, A.; Opatz, T. Org. Lett. 2010, 12, 2140-2141
27. Yang, X. M.; Shi, Q.; Bastow, K. F.; Lee, K. H Org. Lett. 2010, 12, 1416-1419
28. Ambrosini, L. M.; Cernak, T. A.; Lambert, T. H. Tetrahedron 2010, 66, 4882-4887
29. Faber, L.; Wiegrebe, W. Helv. Chim. Acta 1976, 59, 2201-2212
30. Buckley, T. F.; Rapoport, H. J. J. Org. Chem. 1983, 48, 4222-4232
31. Nordlander, J. E.; Njoroge, F. G. J. Org. Chem. 1987, 52, 1627-1630
32. Comins, D. L.; Chen, X.; Morgan, L. A. J. Org. Chem. 1997, 62, 7435-7438
33. Ihara, M.; Takino, Y.; Tomotake, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1990, 2287-2292
34. Suzuki, H.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1995, 60, 6114-6122
35. David, D.; Stéphane, L.; Axel, C.; Eric, D.; Pierre, G. Eur. J. Org. Chem. 2010, 1943-1950
36. An, T. Y.; Huang, R. Q.; Yang, Z.; Zhang, D. K.; Li, G. R.; Yao, Y. C.; Gao, J. Phytochemistry 2001, 58, 1267-1269
37. Jin, Z.; Li, S. P.; Wang, Q. M.; Huang, R. Q. Chin. Chem. Lett. 2004, 15 (10) 1164-1166
38. Wang, K. L.; Lü, M. Y.; Wang, Q. M.; Huang, R. Q. Tetrahedron 2008, 64, 7504-7510
39. Wang, K. L.; Lü, M. Y.; Yu, A.; Zhu, X. Q.; Wang, Q. M. J. Org. Chem. 2009, 74, 935-938
40. Cui, M. B.; Wang, Q. M. Eur. J. Org. Chem. 2009, 5445-5451
41. Wang, Z. W.; Li, Z.; Wang, K. L.; Wang, Q. M. Eur. J. Org. Chem. 2010, 292-299
42. Wang, Z. W.; Wang, Q. M. Tetrahedron Lett. 2010, 51, 1377-1379
43. Wang, K. L.; Su, B.; Wang, Z. W.; Wu, M.; Li, Z.; Hu, Y. N.; Fan, Z. J.; Mi, N.; Wang, Q. M. J. Agric. Food Chem. 2010, 58 (5) 2703-2709
44. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726-3748
45. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175
46. Houk, K. N.; List, B. Acc. Chem. Res. 2004, 37, 487
47. For a review of proline-catalyzed asymmetric reactions, see: List, B. Tetrahedron 2002, 58, 5573-5590
48. Casas, J.; Engqvist, M.; Ibrahem, I.; Kaynak, B.; Cordova, A. Angew. Chem., Int. Ed. 2005, 44, 1343-1345
49. List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395-2396
50. Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799
51. Sabitha, G.; Fatima, N.; Reddy, E. V.; Yadav, J. S. Adv. Synth. Catal. 2005, 347, 1353-1355
52. Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III Synlett 2003, 1910-1914
53. Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 3958-3960
54. For α-functionalization reviews see: Franzen, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T. C.; Kjærsgaard, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 18296-18304
55. Guillena, G.; Ramon, D. J. Tetrahedron: Asymmetry 2006, 17, 1465-1492
56. Merino, P.; Tejero, T. Angew. Chem., Int. Ed. 2004, 43, 2995-2997
57. Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250
58. Brown, S. P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 10808-10809
59. Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Shoji, M. Tetrahedron Lett. 2003, 44, 8293-8296
60. Zhong, G.; Yu, Y. Org. Lett. 2004, 6, 1637-1639
61. Kondekar, N. B.; Kumar, P. Org. Lett. 2009, 11, 2611-2614
62. Levine, S. G. J. Am. Chem. Soc. 1958, 80, 6150-6151
63. Bremmer, M. L.; Khatri, N. A.; Weinreb, S. M. J. Org. Chem. 1983, 48, 3661-3666