A concise approach for the total synthesis of pseudolaric acid A

Organic Letters

Volumn 13, Issue 10, 2011, Pages 2630-2633

  Xu, Tao ^a   Li, Chuang Chuang ^a   Yang, Zhen ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; DITERPENE; IODIDE; PSEUDOLARIC ACID A; SAMARIUM; SAMARIUM DIIODIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; PINACEAE; STEREOISOMERISM; SYNTHESIS;

BIOLOGICAL PRODUCTS; CYCLIZATION; DITERPENES; IODIDES; MOLECULAR STRUCTURE; PINACEAE; SAMARIUM; STEREOISOMERISM;

EID: 79956089011     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200741j     Document Type: Article

References (59)

1. Chiu, P.; Leunga, L. T.; Kob, B. C. B. Nat. Prod. Rep. 2010, 27, 1066
2. Ni, G.-P. Zhongguo Zhongyao Zazhi 1957, 3, 156
3. Wu, J. X.; Hu, R. S.; Yang, G. L. Chin. J. Dermatol. 1960, 8, 18
4. Yao, J.; Lin, X. Acta Chim. Sin. 1982, 40, 385
5. Ying, B.; Xu, R.; Mi, J.; Han, J. Acta Chim. Sin. 1988, 46, 85
6. Geng, Z.; Chen, B.; Chiu, P. Angew. Chem., Int. Ed. 2006, 45, 6197
7. Trost, B. M.; Waser, J.; Meyer, A. J. Am. Chem. Soc. 2007, 129, 14556
8. Trost, B. M.; Waser, J.; Meyer, A. J. Am. Chem. Soc. 2008, 130, 16424
9. Pan, B.; Chang, H.; Cai, G.; Guo, Y. Pure Appl. Chem. 1989, 61, 389
10. Hu, Y.; Ou, L.; Bai, D. Tetrahedron Lett. 1999, 40, 545
11. Hu, Y. H.; Ou, L. G.; Wang, X. L.; Bai, D. L. Chin. Chem. Lett. 1999, 10, 281
12. Ou, L.; Hu, Y.; Song, G.; Bai, D. Tetrahedron 1999, 55, 13999
13. Jiang, X. T.; Ou, L. G.; Han, D. M.; Zhai, Y. F.; Bai, D. L. Chin. Chem. Lett. 2001, 12, 113
14. Wu, B.; Karle, J. M.; Watkins, E. B.; Avery, M. A. Tetrahedron Lett. 2002, 43, 4095
15. L. A. Paquette, L. A.; Pettigrew, J. D. Synthesis 2009, 379
16. Pettigrew, J. D.; Paquette, L. A. Heterocycles 2010, 99
17. 2-induced transformations, see: Molander, A. G.; Harris, C. R. Tetrahedron 1998, 54, 3321
18. Molander, A. G.; Harris, C. R. Chem. Rev. 1996, 96, 307
19. Edmonds, D. J.; Johnson, D.; Procter, D. J. Chem. Rev. 2004, 104, 3371
20. Grubbs, R. H.; Fu, G. C. J. Am. Chem. Soc. 1992, 114, 5426
21. Grubbs, R. H.; Schwab, P.; France, M. B.; Ziller, J. W. Angew. Chem., Int. Ed. 1995, 34, 2039
22. Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; Dimare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875
23. Bazan, G. C.; Oskam, J. H.; Cho, H.-N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899
24. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371
25. Procter, D. J.; Flowers, R. A., II; Skrydstrup, T. Organic Synthesis using Samarium Diiodide: A Practical Guide; RSC Publishing: Cambridge, 2010.
26. Nicolaou, K. C.; Ellery, S. P.; Chen, J. S. Angew. Chem., Int. Ed. 2009, 48, 7140
27. Edmonds, D. J.; Johnston, D.; Procter, D. J. Chem. Rev. 2004, 104, 3371
28. Cui, K.; Liao, H.; Yao, Z. 11th Tetrahedron Symposium, 2010, Beijing, China, PSC113
29. Wei, G. 18th IUPAC International Conference on Organic Synthesis, Bergen, Norway, 2010, Poster No. 032-543.
30. Tannert, R.; Milroy, L.-G.; Ellinger, B.; Hu, T.-S.; Arndt, H.-D.; Waldmann, H. J. Am. Chem. Soc. 2010, 132, 3063
31. Smith, A. B., III; Bosanac, T.; Basu, K. J. Am. Chem. Soc. 2009, 131, 2348
32. Fürstner, A.; Nevado, C.; Waser, M.; Tremblay, M.; Chevrier, C.; Teply, F.; Ai'ssa, C.; Moulin, E.; Müller, O. J. Am. Chem. Soc. 2007, 129, 9150
33. Trost, B. M.; Dong, G.; Vance, J. A. J. Am. Chem. Soc. 2007, 129, 4540
34. Li, Y,l; Hale, K. J. Org. Lett. 2007, 9, 1267
35. Yang, Z. Q.; Geng, X.; Solit, D.; Pratilas, C. A.; Rosen, N.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 7881
36. Rheenen, V. V. Tetrahedron Lett. 1969, 985
37. Nitta, I.; Haruyama, T.; Fujimori, S.; Inoue, S.; Ueno, H. Bull. Chem. Soc. Jpn. 1985, 58, 1081
38. Otera, J.; Danoh, N.; Nozaki, H. J. Org. Chem. 1991, 56, 5307
39. Snider, B. B.; Dombroski, M. A. J. Org. Chem. 1987, 52, 5487
40. Wu, F.; Hong, R.; Khan, J.; Liu, X.; Deng, L. Angew. Chem., Int. Ed. 2006, 45, 4301
41. Hermann, K.; Wynberg, H. J. Org. Chem. 1979, 44, 2238
42. Hutton, T. K.; Wuir, K. W.; Procter, D. J. Org. Lett. 2003, 5, 4811
43. Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265
44. Enholm, E. J.; Satici, H.; Trivellas, A. J. Org. Chem. 1989, 54, 5841
45. Enholm, E. J.; Satici, H.; Trivellas, A. J. Org. Chem. 1994, 54, 5841
46. Suzuki, K.; Nakata, T. Org. Lett. 2002, 4, 3943
47. Flowers, R. A., II. Synlett 2008, 1427
48. Dahlen, A.; Hilmersson, G. Eur. J. Inorg. Chem. 2004, 3393
49. Hutton, T. K.; Muir, K.; Procter, D. J. Org. Lett. 2002, 4, 2345
50. Inui, M.; Nakazaki, A.; Kobayashi, S. Org. Lett. 2007, 9, 469
51. Choi, T.-L.; Lee, C. W.; Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 10417
52. Wang, Y.; Romo, D. Org. lett. 2002, 4, 3231
53. Morita, A.; Kuwahara, S. Tetrahedron Lett. 2007, 48, 3163
54. Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413
55. Verma, V. A.; Arasappan, A.; Njoroge, F. G. Tetrahedron Lett. 2010, 51, 4284
56. Kaufman, T. S. Synlett 1997, 1377
57. Johnson, C. R.; Medich, J. R. J. Org. Chem. 1988, 53, 4131
58. Majetich, G.; Grove, J. L. Org. Lett. 2009, 11, 2904
59. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639