An efficient total synthesis of 5-(S)-HETE

Tetrahedron

Volumn 52, Issue 19, 1996, Pages 6635-6646

  Gueugnot, Sylvie ^a   Alami, Mouâd ^a   Linstrumelle, Gérard ^a   Mambu, Lengo ^b   Petit, Yves ^b   Larchevêque, Marc ^b  

^a ECOLE NORMALE SUPÉRIEURE   (France)

^b PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

5 HYDROXYICOSATETRAENOIC ACID;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL;

EID: 0029986525     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00316-X     Document Type: Article

References (52)

1. (a) Nicolaou, K. C.; Ramphal, J. Y.; Petasis, N. A.; Serhan, C. N. Angew. Chem. Int. Ed. Engl. 1991, 30, 1100-1116.
2. (b) Clissold, D.; Thickitt, C. Natural Product Reports 1994, 11, 621-637.
3. For synthesis of 5-HETE see: (a) Corey, E.J.; Albright, J.O.; Barton, A.E.; Hashimoto, S.I. J. Am. Chem. Soc. 1980, 102, 1435-1436.
4. (b) Baldwin, J.E.; Reed, N.V.; Thomas, E.J. Tetrahedron 1981, 37, 263-267.
5. (c) Rokach, J.; Adams, J.; Perry, R. Tetrahedron Lett. 1983, 24, 5185-5188.
6. (d) Corey, E.J.; Hashimoto, S.I. Tetrahedron Lett. 1981, 22, 299-302.
7. (e) Zamboni, R.; Rokach, J. Tetrahedron Lett. 1983, 24, 999-1002.
8. (f) Nicolaou, K.C.; Ladduwahetty, T.; Taffer, I.M.; Zipkin, R.E. Synthesis 1986, 344-347.
9. (g) Shimazaki, T.; Kobayashi, Y.; Sato, F. Chem. Lett. 1988, 1785-1788.
10. (h) Donaldson, W.A.; Tao, C. Synlett. 1991, 895-897.
11. (i) Donaldson, W.A.; Tao, C; Bennett, D.W.; Grubisha, D.S. J. Org. Chem. 1991, 56, 4563-4566.
12. (a) Chemin, D.; Linstrumelle, G. Tetrahedron 1992, 48, 1943-1952.
13. (b) Chemin, D.; Alami, M.; Linstrumelle, G. Tetrahedron Lett. 1992, 33, 2681-2684.
14. (c) Alami, M.; Crousse, B.; Linstrumelle, G.; Mambu, L.; Larchevêque, M. Synlett 1993, 217-218 and references therein.
15. Jeffery, T.; Gueugnot, S.; Linstrumelle, G. Tetrahedron Lett. 1992, 33, 5757-5760.
16. (a) Gao, Y.; Hanson, R.M.;Klunder, J.M.; Ko, S.Y.; Masamune, H.; Sharpless, K.B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
17. (b) Kobayashi, Y.; Shimazaki, T.; Tagushi, H.; Sato, F. J. Org. Chem. 1990, 55, 5324-5335.
18. Ronald, R.C.; Lansinger, J.M.; Lillie, T.S.; Wheeler, C.J. J. Org. Chem. 1982, 47, 2541-2549.
19. Luche, J.L.; Gemal, A.L. J. Am. Chem. Soc. 1981, 103, 5454-5459.
20. For a recent review, see: Alexakis, A.; Mangeney, P. Tetrahedron Asymmetry 1990, 1, 477-510.
21. McNamara, J.M.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 7371-7372 ; Sekisaki, H.; Jung, M.; Kishi, Y. Ibid. 1982, 104, 7372-7374.
22. McNamara, J.M.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 7371-7372 ; Sekisaki, H.; Jung, M.; Kishi, Y. Ibid. 1982, 104, 7372-7374.
23. Bartlett, P.A.; Johnson, W.S.; Eliott, J.D. J. Am. Chem. Soc. 1983, 105, 2088-2089.
24. Johnson, W.S.; Elliott, R.; Elliott, J.D. J. Am. Chem. Soc. 1983, 105, 2904-2905.
25. Wipf, B.; Kupfer, E.; Bertazzi, R.; Georg, H.; Leuenberger, W. Helv. Chim. Acta 1983, 66, 485-488.
26. Seebach, D.; Züger, M.F. Helv. Chim. Acta 1982, 65, 495-503.
27. Larchevêque, M.; Mambu, L.; Petit, Y. Synth. Commun. 1991, 21, 2295-2300.
28. Eliel, E.L. Acc. Chem. Res. 1970, 3, 1-8.
29. Denmark, S.E.; Willson, T.M.; Almstead, N.G. J. Am. Chem. Soc. 1989, 111, 9258-9260.
30. (a) Andrew R.G.; Conrow, R.E.; Elliott, J.D.; Johnson, W.S.; Ramezani, S. Tetrahedron Lett. 1987, 28, 6535-6538.
31. (b) Silverman, I.R.; Edington, C.; Elliott, J.D.; Johnson, W.S. J. Org. Chem. 1987, 52, 180-183.
32. (c) Normant, J.F.; Alexakis, A.; Ghribi, A.; Mangeney, P. Tetrahedron 1989, 45, 507-516.
33. (d) Basile, T.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Chem. Soc. Chem. Commun. 1989, 596-597.
34. (e) Choi, V.M.F.; Elliott, J.D.; Johnson, W.S. Tetrahedron Lett. 1984, 25, 591-594.
35. 4 (0-2M versus 4.5M) affords a 1/9 mixture of primary and secondary alcohols.
36. The enantiomerical purity of the propargylic alcohol 10 was measured by VPC after reaction with i-propylisocyanate (50 m capillary column - XE60-5-valine-S-α-pea: Chrompack) and was found better than 98%.
37. Nicolaou, K.C.; Veale, C.A.; Webber, S.E.; Katerinopoulos, H. J. Am. Chem. Soc. 1985, 105, 7515-7518.
38. Kocienski, P.J.; Gernigliaro, G.; Feldstein, G. J. Org. Chem. 1977, 42, 353-355.
39. (a) Brown, C.A.; Ahuja, V.K. J. Chem. Soc. Chem. Commun 1973, 553-554.
40. (b) Brown, C.A.; Ahuja, V.K. J. Org. Chem. 1973, 38, 2226-2230.
41. Schmidt, H. M.; Arens, J. F. Recl. Trav. Chim. Pays Bas 1967, 86, 1138-1142.
42. (a) Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403-6406.
43. (b) Crousse, B.; Alami, M.; Linstrumelle, G. Tetrahedron Lett. 1995, 36, 4245-4248.
44. (c) Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1994, 35, 3543-3544.
45. Boland, W.; Schroer, N.; Sieler, C.; Feigel, M. Helv. Chim. Acta. 1987, 70, 1025-1040.
46. Guerriero, A.; d'Ambrosio, M.; Pietra, F. Helv. Chim. Acta. 1990, 73, 2183-2189.
47. Doolittle, R.E.; Heath, R.R. J. Org. Chem. 1984, 49, 5041-5050.
48. Huckstep, M.; Taylor, R.J.K.; Caton, M.P.L. Synthesis 1982, 881-882.
49. Corey, E.J.; Danheiser, R.L.; Chandrasekaran, S.; Siret, P.; Keck, G.E.; Gras, J.L. J. Am. Chem. Soc. 1978, 100, 8031-8034.
50. Kerdesky, F.A.J.; Schmidt, S.P.; Holms, J.H.; Dyer, R.D.; Carter, J.W.; Brooks, D.W. J. Med. Chem. 1987, 30, 1177-1186.
51. Myagkova, G.I.; Yakusheva, L.A.; Bordyukova, O.O.; Shatskaya, V.B.; Evstigneeva, R.P. Soviet J. Bio. Chem. 1982, 8, 255-260.
52. Noel, J.P.; Beaucourt, J.P.; Heitz, M.P.; Wagner, A.; Mioskowski, C. J. Org. Chem. 1989, 54, 500-503.