Stereoselective synthesis of chiral tetrahydrofurans with potent 5-LO inhibitory activity

Tetrahedron Asymmetry

Volumn 16, Issue 6, 2005, Pages 1125-1133

  Sharma, G V M ^a   Punna, Sreenivas ^a   Krishna, Palakodety Radha ^a   Chorghade, Mukund S ^b   Ley, Steven V ^c  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b Chorghade Enterprises   (United States)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

5 (4 FLUOROPHENOXYMETHYL) 2 (1 N HYDROXYUREIDYL 3 BUTYN 4 YL)TETRAHYDROFURAN; ETHER DERIVATIVE; LIPOXYGENASE INHIBITOR; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLIZATION; DRUG ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 14944356440     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.01.045     Document Type: Article

References (23)

1. P.J. Barnes, K.F. Chung, and C.P. Page Pharmacol. Rev. 50 1996 515 596
2. R.A. Coleman, M. Johnson, A.T. Nials, and C.J. Vardey Trends Pharmacol. Sci. 17 1996 324 330
3. W.M. Brown Curr. Opin. Antiinflamm. Immunomod. Invest. Drugs 1 1999 64
4. L. Pradello Curr. Opin. Antiinflamm. Immunomod. Invest. Drugs 1 1999 56 60
5. I.M. Adocock, and J.G. Mathews Drug Discovery Today 3 1998 395 399
6. X. Cai, R.T. Scannell, D. Yaegar, M.S. Hussoin, D.B. Killian, C. Qian, J. Eckman, C.G. Yeh, S.-B. Hwang, L.-L. Garahan, S.H. Ip, and T.Y. Shen J. Med. Chem. 41 1998 1970 1979
7. D.F. Rogers, and M.A. Giembycz Trends Pharmacol. Sci. 18 1998 160 164
8. X. Cai, S. Cheah, S.M. Chen, J. Eckmann, J. Ellis, R. Fisher, A. Fura, G. Grewal, S. Hussion, S. Ip, D.B. Killian, L.-L. Garahan, H. Lounsbury, C.G. Qian, R.T. Scannell, D. Yaeger, D.M. Wypij, C.G. Ye, M.A. Young, and S.X. Yu Abstr. Papers Am. Chem. Soc. 214 1997 214-MEDI
9. Cai, X.; Hwang, S.; Killan, D.; Shen, T. Y. U.S. Patent 5,648,486, 1997
10. Cai, X.; Grewal, G.; Hussion, S.; Fura, A.; Biftu, T. U.S. Patent 5,681,966, 1977
11. X. Cai, M.S. Chorghade, A. Fura, G.S. Grewal, K.A. Jauregui, H.A. Lounsbury, R.T. Scannell, C.G. Yeh, M.A. Young, S. Yu, L. Guo, R.M. Moriatry, R. Penmastu, M.S. Rao, R.K. Singhal, Z. Song, J.P. Staszewski, S.M. Tuladhar, and S. Yang Org. Process Res. Dev. 3 1999 73 76
12. Chorghade, M. S.; Gurjar, M. K.; Adhikari, S. S.; Sadalapure, K.; Lalitha, S. V. S.; Murugaiah, A. M. S.; Radhakrishna, P. U.S. Patent Appl. 60/091, 710, 1998
13. M.S. Chorghade, M.K. Gurjar, S.S. Adikari, K. Sadalapure, S.V.S. Lalitha, A.M.S. Murugaiah, and P. Radhakrishna Pure Appl. Chem. 71 1999 1071 1074
14. M.K. Gurjar, L.M. Krishna, B.S. Reddy, and M.S. Chorghade Synthesis 2000 557 560
15. D.J. Dixon, S.V. Ley, D.J. Reynolds, and M.S. Chorghade Indian J. Chem. (B) 40 2001 1043 1053
16. M.K. Gurjar, A.M.S. Murugaiah, P. Radhakrishna, C.V. Ramana, and M.S. Chorghade Tetrahedron: Asymmetry 14 2003 1363 1370
17. M.E. Jung, and T.J. Shaw J. Am. Chem. Soc. 102 1980 6304 6311
18. 4
19. J. Baxter, E.G. Mata, and E.J. Thomas Tetrahedron 54 1998 14359 14376
20. Y. Oikawa, T. Tanaka, K. Horita, T. Yosioka, and O. Yonemitsu Tetrahedron Lett. 25 1984 5393 5396
21. G.V.M. Sharma, T.R. Prasad, P. Radhakrishna, K. Krishnudu, M.H.V.R. Rao, and A.C. Kunwar Tetrahedron: Asymmetry 11 2000 4499 4507
22. A.O. Stewart, and D.W. Brooks J. Org. Chem. 57 1992 5020 5023
23. O. Mitsunobu Synthesis 1981 1 28