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

Chemical Communications

Volumn , Issue 5, 1997, Pages 493-494

  Kobayashi, Yuichi ^a   Shimizu, Kiyoshi ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008549770     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a608429j     Document Type: Short Survey

References (29)

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. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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; G. V. M. Sharma and S. M. Rao, Tetrahedron Lett., 1994, 35, 4231.
9. 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; G. V. M. Sharma and S. M. Rao, Tetrahedron Lett., 1994, 35, 4231.
10. 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; G. V. M. Sharma and S. M. Rao, Tetrahedron Lett., 1994, 35, 4231.
11. 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; G. V. M. Sharma and S. M. Rao, Tetrahedron Lett., 1994, 35, 4231.
12. 14,15-DiHETE: J. R. Falck, S. Manna, 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, 13011.
13. 14,15-DiHETE: J. R. Falck, S. Manna, 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, 13011.
14. P. Jankowski, P. Raubo and J. Wicha, Synlett, 1994, 985.
15. 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; M. Masnyk and J. Wicha, Chem. Ber., 1994, 127, 677; Attempts to give trans allylic alcohols: 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.
16. 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; M. Masnyk and J. Wicha, Chem. Ber., 1994, 127, 677; Attempts to give trans allylic alcohols: 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.
17. 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; M. Masnyk and J. Wicha, Chem. Ber., 1994, 127, 677; Attempts to give trans allylic alcohols: 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.
18. 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; M. Masnyk and J. Wicha, Chem. Ber., 1994, 127, 677; Attempts to give trans allylic alcohols: 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.
19. 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; M. Masnyk and J. Wicha, Chem. Ber., 1994, 127, 677; Attempts to give trans allylic alcohols: 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.
20. Y. Kobayashi, T. Ito, I. Yamakawa, H. Urabe and F. Sato, Synlett, 1991, 813.
21. Y. Kitano, T. Matsumoto and F. Sato, Tetrahedron, 1988, 44, 4073.
22. M. G. Finn and K. B. Sharpless, in Asymmetric Synthesis, ed. J. D. Morrison, Academic, New York, 1985, vol. 5, ch. 8, p. 247.
23. N. Miyaura, K. Yamada, H. Suginome and A. Suzuki, J. Am. Chem. Soc., 1985, 107, 972.
24. (a) Y. Kobayashi, T. Shimazaki, H. Taguchi and F. Sato, J. Org. Chem., 1990, 55, 5324;
25. (b) T. Shimazaki, Y. Kobayashi, F. Sato, T. Iwama and K. Shikada, Prostaglandins, 1990, 39, 459;
26. (c) T. Shimazaki, K. Kawajiri, Y. Kobayashi and F. Sato, Prostaglandins, 1993, 45, 335;
27. (d) Y. Kobayashi, T. Shimazaki, K. Kawajiri, T. Shimizu, Y. Seyama and F. Sato, Biochim. Biophys. Acta, 1994, 1215, 280.
28. (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;
29. (b) P. Westlund, C. Edenius and J. Å. Lindgren, Biochim. Biophys. Acta. 1988, 962, 105.