A new synthetic approach for 4(S)-hydroxycyclopent-2-enone: A precursor to prostanoid synthesis

Tetrahedron Letters

Volumn 46, Issue 37, 2005, Pages 6325-6328

  Chang, Chih Tsung ^a   Jacobo, Sheila H ^a   Powell, William S ^b   Lawson, John A ^c   FitzGerald, Garret A ^c   Pratico, Domenico ^c   Rokach, Joshua ^a  

^a Florida Institute of Technology   (United States)

^b MCGILL UNIVERSITY   (Canada)

^c UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

4(S) Hydroxycyclopent 2 enone; Olefin metathesis; Synthesis

Indexed keywords

4 HYDROXYCYCLOPENT 2 ENONE; KETONE DERIVATIVE; PROSTANOID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; METHODOLOGY; PRECURSOR;

EID: 23744488236     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.035     Document Type: Article

References (36)

1. M. Hetmanski, N. Purcell, R.J. Stoodley, and M.N. Palfreyman J. Chem. Soc., Perkin Trans. 1 1984 2089 2096
2. M. Rowley, and Y. Kishi Tetrahedron Lett. 29 1988 4909 4912
3. H. Nagaoka, T. Miyakoshi, and Y. Yamada Tetrahedron Lett. 25 1984 3621 3624
4. H. Nagaoka, H. Miyaoka, and Y. Yamada Tetrahedron Lett. 31 1990 1573 1576
5. C.J. Forsyth, and J. Clardy J. Am. Chem. Soc. 112 1990 3497 3505
6. T. Tanaka, T. Toru, N. Okamura, A. Hazato, S. Sugiura, K. Manabe, and S. Kurozumi Tetrahedron Lett. 24 1983 4103 4104
7. M. Suzuki, A. Yanagisawa, and R. Noyori Tetrahedron Lett. 25 1984 1383 1396
8. M. Suzuki, A. Yanagisawa, and R. Noyori J. Am. Chem. Soc. 110 1988 4718 4726
9. M. Kolb, L. VanHijfte, and R.E. Ireland Tetrahedron Lett. 29 1988 6769 6772
10. R. Noyori, and M. Suzuki Angew. Chem., Int. Ed. Engl. 23 1984 847 876
11. Z. Pudukulathan, S. Manna, S.W. Hwang, S.P. Khanapure, J.A. Lawson, G.A. FitzGerald, and J. Rokach J. Am. Chem. Soc. 120 1998 11953 11961
12. T. Tanaka, S. Kurozumi, T. Toru, S. Miura, M. Kobayashi, and S. Ishimoto Tetrahedron 32 1976 1713 1718
13. L.A. Mitscher, G.W.I. Clark, and P.B. Hudson Tetrahedron Lett. 19 1978 2553 2556
14. K. Laumen, and M. Schneider Tetrahedron Lett. 25 1984 5875 5878
15. Z. Liu, L. He, and H. Zheng Tetrahedron: Asymmetry 4 1993 2277 2278
16. D. Bhuniya, A.D. Gupta, and V.K. Singh Tetrahedron Lett. 36 1995 2847 2850
17. A.S. Demir, and O. Sesenoglu Tetrahedron: Asymmetry 13 2002 667 670
18. S.R. Ghorpade, K.B. Bastawade, D.V. Gokhale, P.D. Shinde, V.A. Mahajan, U.R. Kalkote, and T. Ravindranathan Tetrahedron: Asymmetry 10 1999 4115 4122
19. R. Noyori, I. Tomino, M. Yamada, and M. Nishizawa J. Am. Chem. Soc. 106 1984 6717 6725
20. K. Ogura, M. Yamashita, and G. Tsuchihashi Tetrahedron Lett. 10 1976 759 762
21. M. Gill, and R.W. Rickards Tetrahedron Lett. 20 1979 1539 1542
22. M. Nara, S. Terashima, and S. Yamada Tetrahedron 36 1980 3161 3170
23. M. Kitamura, K. Manabe, R. Noyori, and H. Takaya Tetrahedron Lett. 28 1987 4719 4720
24. M. Asami Bull. Chem. Soc. Jpn. 63 1990 1402
25. J.L. Leighton, and E.N. Jacobsen J. Org. Chem. 61 1996 389 390
26. S.P. Khanapure, N. Najafi, S. Manna, J.-J. Yang, and J. Rokach J. Org. Chem. 60 1995 7548 7551
27. A. Srikrishna, and M. Srinivasa-Rao Synlett 2 2004 374 376
28. A. Srikrishna, M. Srinivasa-Rao, S.J. Gharpure, and N. Chandrasekhar-Babu Synlett 12 2001 1986 1988
29. R.H. Grubbs, and S. Chang Tetrahedron 54 1998 4413 4450
30. C. Storm-Poulsen, and R. Madsen Synthesis 1 2003 1 18
31. S.K. Armstrong J. Chem. Soc., Perkin Trans. 1 2 1998 371 388
32. J. Adams, B.J. Fitzsimmons, and J. Rokach Tetrahedron Lett. 25 1984 4713 4716
33. 3): δ 207.1, 163.7, 135.8, 70.7, 44.2.
34. P. Schwab, R.H. Grubbs, and J.W. Ziller J. Am. Chem. Soc. 118 1996 100 110
35. S.T. Nguyen, and R.H. Grubbs J. Am. Chem. Soc. 115 1993 9858 9859
36. C.W. Lee, and R.H. Grubbs Org. Lett. 2 2000 2145 2147