Epoxide ring opening of α,β-epoxysilanes with prop-2-ynyl sulfide dianion—synthesis of (11R,12S,5Z,7E,9E,14Z )-dihydroxyeicosa-5,7,9,14-tetraenoic acid

Abstract

A new methodology for synthesis of lipoxygenase metabolites possessing vic-diol substructures coupled with the conjugated alkene system is developed and successfully applied to the synthesis of (11R,12S,5Z,7E,9E,14Z )-di-hydroxyeicosa-5,7,9,14-tetraenoic acid (DiHETE).

References

1. Recent reviews: W. König, W. Schönfeld, M. Raulf, M. Köller, J. Knöller, J. Scheffer and J. Brom, Eicosanoids, 1990, 3, 1; T. Shimizu and L. S. Wolfe, J. Neurochem., 1990, 55, 1.
2. Reviews: (a) J. Rokach, Y. Guindon, R. N. Young, J. Adams and J. G. Atkinson, in The Total Synthesis of Natural Products, ed. J. ApSimon, Wiley, New York, 1988, vol. 7, p. 141; (b) F. Sato and Y. Kobayashi, Synlett, 1992, 849.
3. 5,6-DiHETE: K. C. Nicolaou, J. Y. Ramphal, J. M. Palazon and R. A. Spanevello, Angew. Chem., Int. Ed. Engl., 1989, 28, 587; A. Gigou, J.-P. Lellouche, J.-P. Beaucourt, L. Toupet and R. Grée, Angew. Chem., Int. Ed. Engl., 1989, 28, 755; C. Kugel, J.-P. Lellouche, J.-P. Beaucourt, G. Niel, J.-P. Girard and J.-C. Rossi, Tetrahedron Lett., 1989, 30, 4947.
4. 11,12-DiHETE: (a) P. Westlund, J. Palmblad, J. R. Falck and S. Lumin, Biochim. Biophys. Acta, 1991, 1081, 301; (b) A. Gigou, J.-P. Beaucourt, J.-P. Lellouche and R. Grée, Tetrahedron Lett., 1991, 32, 635; (c) J. P. Lellouche, A. Gigou-Barbedette and R. Grée, Bull. Soc. Chim. Fr., 1992, 129, 605; (d) G. V. M. Sharma and S. M. Rao, Tetrahedron Lett., 1994, 35, 4231.
5. 14, 15-DiHETE: J. R. Falck, S. Mannal, J. Capdevila and J. D. Buynak, Tetrahedron Lett., 1983, 24, 5719; O. Radmark, C. Serhan, M. Hamberg, U. Lundberg, M. D. Ennis, G. L. Bundy, T. D. Oglesby, P. A. Aristoff, A. W. Harrison, G. Slomp, T. A. Scahill, G. Weissmann and B. Samuelsson, J. Biol. Chem., 1984, 259, 13 011.
6. P. Jankowski, P. Raubo and J. Wicha, Synlett, 1994, 985.
7. Reaction of epoxy silanes and α-sulfonyl anions affords cis allylic alcohols: (a) M. Masnyk and J. Wicha, Tetrahedron Lett., 1988, 29, 2497; (b) S. Marczak, M. Masnyk and J. Wicha, Liebigs Ann. Chem., 1990, 345; (c) M. Masnyk and J. Wicha, Chem. Ber., 1994, 127, 677Attempts to give trans allylic alcohols: (d) P. Jankowski, S. Marczak, M. Masnyk and J. Wicha, J. Organomet. Chem., 1991, 403, 49; (e) B. Achmatowicz, P. Raubo and J. Wicha, J. Org. Chem., 1992, 57, 6593.
8. Y. Kobayashi, T. Ito, I. Yamakawa, H. Urabe and F. Sato, Synlett, 1991, 813.
9. Y. Kitano, T. Matsumoto and F. Sato, Tetrahedron, 1988, 44, 4073.
10. M. G. Finn and K. B. Sharpless, in Asymmetric Synthesis, ed. J. D. Morrison, Academic, New York, 1985, vol. 5, ch. 8, p. 247.
11. N. Miyaura, K. Yamada, H. Suginome and A. Suzuki, J. Am. Chem. Soc., 1985, 107, 972.
12. (a) Y. Kobayashi, T. Shimazaki, H. Taguchi and F. Sato, J. Org. Chem., 1990, 55, 5324; (b) T. Shimazaki, Y. Kobayashi, F. Sato, T. Iwama and K. Shikada, Prostaglandins, 1990, 39, 459; (c) T. Shimazaki, K. Kawajiri, Y. Kobayashi and F. Sato, Prostaglandins, 1993, 45, 335; (d) Y. Kobayashi, T. Shimazaki, K. Kawajiri, T. Shimizu, Y. Seyama and F. Sato, Biochim. Biophys. Acta, 1994, 1215, 280.
13. (a) I. Miki, T. Shimizu, Y. Seyama, S. Kitamura, K. Yamaguchi, H. Sano, H. Ueno, A. Hiratsuka and T. Watabe, J. Biol. Chem., 1989, 264, 5799; (b) P. Westlund, C. Edenius and J. Å. Lindgren, Biochim. Biophys. Acta, 1988, 962, 105.