A key intermediate towards oxylipins. A formal synthesis of (12S)-HETE and (12S)-LTB4

Journal of Chemical Research - Part S

Volumn , Issue 2, 1999, Pages 104-105

  Benkouider, Abdelhamid ^a   Pale, Patrick ^b  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 PROPANEDIOL; 3 METHOXYMETHOXYUNDEC 5 EN 1 YNE; ACETYLENE DERIVATIVE; FATTY ACID DERIVATIVE; OXYLIPIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; METABOLITE; OPTICAL ROTATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033020618     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807074a     Document Type: Article

References (24)

1. W. H. Gerwick, Chem. Rev., 1993, 93, 1807.
2. W. H. Gerwick and M. W. Bernart, Eicosanoids and related compounds from marine algae, in Marine Biotechnology, Vol. I: Pharmaceutical and bioactive natural products, ed. D. H. Attaway and O. R. Zaborsky, Plenum, New York, 1992, p. 101.
3. D. Grandjean, P. Pale and J. Chuche, Tetrahedron, 1991, 47, 1215.
4. A. Benkouider, PhD Thesis, 1994, University of Reims-Champagne-Ardenne, Reims; C. Barloy-Da Silva, PhD Thesis, 1998, University L. Pasteur, Strasbourg.
5. A. Benkouider, PhD Thesis, 1994, University of Reims-Champagne-Ardenne, Reims; C. Barloy-Da Silva, PhD Thesis, 1998, University L. Pasteur, Strasbourg.
6. (a) Constanolactones: D. G. Nagle and W. H. Gerwick, J. Org. Chem., 1994, 59, 7227; Tetrahedron Lett., 1989, 31, 2995;
7. (a) Constanolactones: D. G. Nagle and W. H. Gerwick, J. Org. Chem., 1994, 59, 7227; Tetrahedron Lett., 1989, 31, 2995;
8. (b) Solandelactones: Y. Seo, K. W. Cho, J.-R. Rho, J. Shin, B.-M. Kwon, S.-H. Bok and J.-I. Song, Tetrahedron, 1996, 52, 10583;
9. (c) 12 S-HETE and 6E-LTB4: M. W. Bernart and W. H. Gerwick, Phytochemistry, 1994, 36, 1233.
10. For other synthetic approaches towards these lactones, see: S. Varadarajan, D. K. Mohapatra and A. Datta, Tetrahedron Lett., 1998, 39, 5667; H. Miyaoka, T. Shigemoto and Y. Yamada, Heterocycles, 1998, 47, 415; J. D. White and M. S. Jensen, J. Am. Chem. Soc., 1995, 117, 6224; T. Nagasawa, Y. Onoguchi, T. Matsumoto and K. Suzuki, Synlett, 1995, 1023.
11. For other synthetic approaches towards these lactones, see: S. Varadarajan, D. K. Mohapatra and A. Datta, Tetrahedron Lett., 1998, 39, 5667; H. Miyaoka, T. Shigemoto and Y. Yamada, Heterocycles, 1998, 47, 415; J. D. White and M. S. Jensen, J. Am. Chem. Soc., 1995, 117, 6224; T. Nagasawa, Y. Onoguchi, T. Matsumoto and K. Suzuki, Synlett, 1995, 1023.
12. For other synthetic approaches towards these lactones, see: S. Varadarajan, D. K. Mohapatra and A. Datta, Tetrahedron Lett., 1998, 39, 5667; H. Miyaoka, T. Shigemoto and Y. Yamada, Heterocycles, 1998, 47, 415; J. D. White and M. S. Jensen, J. Am. Chem. Soc., 1995, 117, 6224; T. Nagasawa, Y. Onoguchi, T. Matsumoto and K. Suzuki, Synlett, 1995, 1023.
13. For other synthetic approaches towards these lactones, see: S. Varadarajan, D. K. Mohapatra and A. Datta, Tetrahedron Lett., 1998, 39, 5667; H. Miyaoka, T. Shigemoto and Y. Yamada, Heterocycles, 1998, 47, 415; J. D. White and M. S. Jensen, J. Am. Chem. Soc., 1995, 117, 6224; T. Nagasawa, Y. Onoguchi, T. Matsumoto and K. Suzuki, Synlett, 1995, 1023.
14. For another approach towards these lactones, see: S. Varadarajan, D. K. Mohapatra and A. Datta, Tetrahedron Lett.. 1998, 39, 1075.
15. For related synthesis of eicosanoids, see: (a) D. Chemin and G. Linstrumelle, Tetrahedron, 1992, 48, 1943;
16. (b) K. C. Nicolaou, J. Y. Ramphal, N. A. Petasis and C. N. Serhan, Angew. Chem., Int. Ed., 1991, 30, 1100.
17. M. Treilhou, A. Fauve, J.-R. Pougny, J. C. Promé and H. Veschambre, J. Org. Chem., 1992, 57, 3203.
18. K. C. Nicolaou, J. Y. Ramphal and Y. Abe, Synthesis, 1989, 898.
19. P. Pianetti, P. Rollin and J.-R. Pougny, Tetrahedron Lett., 1986, 27, 5853.
20. (a) H. C. Brown and P. V. Ramachandran, Acc. Chem. Res., 1992, 25, 16;
21. (b) M. M. Midland, A. J. Tramontano, A. Kazubski, R. S. Graham, D. J. S. Tsai and D. B. Cardin, Tetrahedron, 1984, 40, 1371; M. M. Midland and R. S. Graham, Org. Synth., 1984, 63, 57;
22. (b) M. M. Midland, A. J. Tramontano, A. Kazubski, R. S. Graham, D. J. S. Tsai and D. B. Cardin, Tetrahedron, 1984, 40, 1371; M. M. Midland and R. S. Graham, Org. Synth., 1984, 63, 57;
23. (c) C. Helal and E. J. Corey, Tetrahedron Lett., 1995, 36, 9153;
24. (d) C. J. Helal, P. A. Magriotis and E. J. Corey, J. Am. Chem. Soc., 1996, 118, 10938.