Sequential Pd(0)-, Rh(I)-, and Ru(II)-catalyzed reactions in a nine-step synthesis of clinprost

Organic Letters

Volumn 15, Issue 3, 2013, Pages 586-589

  Nagy, Emma E ^a   Hyatt, I F Dempsey ^a   Gettys, Kristen E ^a   Yeazell, Shawn T ^a   Frempong, Stephen K ^a   Croatt, Mitchell P ^a  

^a UNIVERSITY OF NORTH CAROLINA AT GREENSBORO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84873339333     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol303402e     Document Type: Article

References (50)

1. Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc. Chem. Res. 2007, 41, 40
2. Moncada, S.; Gryglewski, R.; Bunting, S.; Vane, J. R. Nature 1976, 263, 663
3. Johnson, R. A.; Morton, D. R.; Kinner, J. H.; Gorman, R. R.; McGuire, J. C.; Sun, F. F.; Whittaker, N.; Bunting, S.; Salmon, J.; Moncada, S.; Vane, J. R. Prostaglandins 1976, 12, 915
4. Forfia, P. R.; McLaughlin, V. V. Medical Treatment of PAH: Prostacyclins. In Pulmonary Hypertension; Informa Healthcare: New York, 2009; p 338.
5. Matsuda, S.; Wen, T.-C.; Karasawa, Y.; Araki, H.; Otsuka, H.; Ishihara, K.; Sakanaka, M. Brain Res. 1997, 769, 321
6. Minagawa, T.; Sakanaka, K.; Inaba, S.-I.; Sai, Y.; Tamai, I.; Suwa, T.; Tsuji, A. J. Pharm. Pharmacol. 1996, 48, 1016
7. Sheddan, N. A.; Mulzer, J. Org. Lett. 2006, 8, 3101
8. Hemmerle, H.; Gais, H.-J. Angew. Chem., Int. Ed. Engl. 1989, 28, 349
9. Sheddan, N. A.; Mulzer, J. Org. Biomol. Chem. 2006, 4, 4127
10. Ishikawa, T.; Ishii, H.; Shimizu, K.; Nakao, H.; Urano, J.; Kudo, T.; Saito, S. J. Org. Chem. 2004, 69, 8133
11. Hashimoto, S.-i.; Shinoda, T.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1988, 1137
12. Sodeoka, M.; Ogawa, Y.; Mase, T.; Shibasaki, M. Chem. Pharm. Bull. 1989, 37, 586
13. Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, K.; Kurozumi, S. Tetrahedron Lett. 1986, 27, 6353
14. Hashimoto, S.-i.; Kase, S.; Shinoda, T.; Ikegami, S. Chem. Lett. 1989, 18, 1063
15. Hashimoto, S.-i.; Shinoda, T.; Shimada, Y.; Honda, T.; Ikegami, S. Tetrahedron Lett. 1987, 28, 637
16. Torisawa, Y.; Okabe, H.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1984, 1602
17. Torisawa, Y.; Okabe, H.; Shibasaki, M.; Ikegami, S. Chem. Lett. 1984, 13, 1069
18. Shibasaki, M.; Torisawa, Y.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3493
19. Mase, T.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 5087
20. Sodeoka, M.; Shibasaki, M. Chem. Lett. 1984, 13, 579
21. Ogawa, Y.; Shibasaki, M. Tetrahedron Lett. 1984, 25, 1067
22. Suzuki, M.; Koyano, H.; Noyori, R. J. Org. Chem. 1987, 52, 5583
23. Mandai, T.; Matsumoto, S.; Kohama, M.; Kawada, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671
24. Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K.; Tomimori, K.; Kato, Y.; Kurozumi, S.; Noyori, R. Tetrahedron 1990, 46, 6689
25. Tanaka, T.; Bannai, K.; Hazato, A.; Koga, M.; Kurozumi, S.; Kato, Y. Tetrahedron 1991, 47, 1861
26. Park, H.; Lee, Y. S.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 86
27. Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur. J. Org. Chem. 1998, 1998, 1319
28. Touré, B. B.; Hall, D. G. Chem. Rev. 2009, 109, 4439
29. Das, S.; Chandrasekhar, S.; Yadav, J. S.; Grée, R. Chem. Rev. 2007, 107, 3286
30. Sheddan, N. A.; Czybowski, M.; Mulzer, J. Chem. Commun. 2007, 2107
31. Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948
32. Croatt, M. P.; Wender, P. A. Eur. J. Org. Chem. 2010, 2010, 19
33. Crilley, M. M. L.; Golding, B. T.; Pierpoint, C. J. Chem. Soc., Perkin Trans. 1 1988, 2061
34. Lee, P.-H.; Shim, E.-K.; Lee, K.-Y.; SeoMoon, D.; Kim, S.-D. Bull. Korean Chem. Soc. 2005, 26, 157
35. Evans, P. A.; Leahy, D. K. J. Am. Chem. Soc. 2003, 125, 8974
36. Andersson, P. G.; Baeckvall, J. E. J. Org. Chem. 1991, 56, 5349
37. Sato, Y.; Oonishi, Y.; Mori, M. J. Org. Chem. 2003, 68, 9858
38. Gruber, S.; Zaitsev, A. B.; Wörle, M.; Pregosin, P. S.; Veiros, L. F. Organometallics 2008, 27, 3796
39. Rodriguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030
40. Weaver, J. D.; Recio, A.; Grenning, A. J.; Tunge, J. A. Chem. Rev. 2011, 111, 1846
41. Tsuda, T.; Chujo, Y.; Nishi, S.; Tawara, K.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 6381
42. Rayabarapu, D. K.; Tunge, J. A. J. Am. Chem. Soc. 2005, 127, 13510
43. Pi, S.-F.; Tang, B.-X.; Li, J.-H.; Liu, Y.-L.; Liang, Y. Org. Lett. 2009, 11, 2309
44. Sim, S. H.; Park, H.-J.; Lee, S. I.; Chung, Y. K. Org. Lett. 2008, 10, 433
45. Torregrosa, R. R. P.; Ariyarathna, Y.; Chattopadhyay, K.; Tunge, J. A. J. Am. Chem. Soc. 2010, 132, 9280
46. Zhang, W.-W.; Zhang, X.-G.; Li, J.-H. J. Org. Chem. 2010, 75, 5259
47. Nugent, W. A. Angew. Chem., Int. Ed. 2012, 51, 8936
48. As stated in the following reference, a Black Swan Event must have three attributes: "rarity, extreme impact, and retrospective (though not prospective) predictability".
49. Taleb, N. N. The Black Swan: Impact of the Highly Improbable, 2 nd ed.; The Random House Publishing Group: New York, 2010.
50. Felluga, F.; Forzato, C.; Ghelfi, F.; Nitti, P.; Pitacco, G.; Pagnoni, U. M.; Roncaglia, F. Tetrahedron: Asymmetry 2007, 18, 527