Fluorine-containing butanolides and butenolides. Vinylic fluorine displacement in 4,4-dialkyl-2,3-difluoro-2-buten-4-olides and a novel rearrangement induced by organolithium addition to a carbonyl group

Tetrahedron

Volumn 56, Issue 20, 2000, Pages 3197-3207

  Paleta, Oldřich ^a   Pelter, Andrew ^b   Kebrle, Josef ^a   Duda, Zdeněk ^a   Hajduch, Jan ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^b SWANSEA UNIVERSITY   (United Kingdom)

Author keywords

Butanolides; Butenolides; Hard and soft nucleophiles; Organo lithium addition rearrangement; Vinylic fluorine displacement

Indexed keywords

BUTANOLIDE DERIVATIVE; BUTENOLIDE; BUTENOLIDE DERIVATIVE; CARBONYL DERIVATIVE; FLUORINE DERIVATIVE; ORGANOLITHIUM COMPOUND; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0034640468     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00167-8     Document Type: Article

References (69)

1. Knight D.W. Contemp. Org. Synth. 1:1994;287.
2. Pelter A., Al-Bayati R.I.H., Ayoub M.T., Lewis W., Pardasani P., Hansel R. J. Chem. Soc., Perkin Trans. 1. 1987;717.
3. Pelter A., Hansel R. Z. Naturforsch. Teil B. 27b:1972;1186.
4. Hansel R., Schultz J. Z. Naturforsch. Teil B. 33b:1978;688.
5. Pelter A., Al-Bayati R.I.H., Hansel R., Dinter H., Burke B. Tetrahedron Lett. 22:1981;1545.
6. Pfander, H. Key to Carotenoids (2nd ed.); Birkhaeuser: Basel, 1987; Foss, P.; Guillard, R. R. L.; Liaaen-Jensen, S. Phytochemistry 1986, 25, 119.
7. Pfander, H. Key to Carotenoids (2nd ed.); Birkhaeuser: Basel, 1987; Foss, P.; Guillard, R. R. L.; Liaaen-Jensen, S. Phytochemistry 1986, 25, 119.
8. Triozze P.L., Ailabouni J., Rinehart J.J., Witiak D.T. Int. J. Pharmacol. 15:1993;47.
9. Fang X.P., Anderson J.E., Smith D.L., McLaughlin J.L., Wood K.V. J. Nat. Prod. 55:1992;1655.
10. Mori H., Yoshimi N., Sugie S., Tanaka T., Morishita Y., Jinlong G., Tamai Y., Torihara M., Yamahara J. Cancer Lett. 66:1992;93. (Shannon, Irel.).
11. Roggo, B. E.; Hug, P.; Moss, S; Raschorf, F.; Peter, H. H. J. Antibiot., 1994, 47, 143; Roggo, B. E.; Petersen, F.; Delmendo, R.; Jenny, H. B.; Peter, H. H.; Roesel, J. J. J. Antibiot., 1994, 47, 136.
12. Roggo, B. E.; Hug, P.; Moss, S; Raschorf, F.; Peter, H. H. J. Antibiot., 1994, 47, 143; Roggo, B. E.; Petersen, F.; Delmendo, R.; Jenny, H. B.; Peter, H. H.; Roesel, J. J. J. Antibiot., 1994, 47, 136.
13. Fang, X.-P.; Anderson, J. E.; Chang, C.-J.; McLaughlin, J. L. Tetrahedron, 1991, 47, 9751; Ruprecht, J. K.; Hui, Y. H.; McLaughlin, J. L. J. Nat. Prod., 1990, 53, 237
14. Fang, X.-P.; Anderson, J. E.; Chang, C.-J.; McLaughlin, J. L. Tetrahedron, 1991, 47, 9751; Ruprecht, J. K.; Hui, Y. H.; McLaughlin, J. L. J. Nat. Prod., 1990, 53, 237
15. Tuchinda P., Udchachon J., Reutrakul V., Santisuk T., Taylor W.C., Farnsworth N.R., Pezzuto J.M., Kinghorn A.D. Phytochem. 30:1991;2685.
16. Ito M. Pure Appl. Chem. 63:1991;13.
17. Nishino H., Satomi Y., Tokuda H., Nishino A., Iwashima A., Tanaka Y., Zamano Y., Shibata Y., Torihara M. Kyoto-furitsu Ika Daigaku Zasshi. 100:1991;831. Chem. Abstr., 1992, 116, 50881.
18. Nishino H., Satomi Y., Tokuda H., Nishino A., Iwashima A., Tanaka Y., Zamano Y., Shibata Y., Torihara M. Kyoto-furitsu Ika Daigaku Zasshi. 100:1991;831. Chem. Abstr., 1992, 116, 50881.
19. Semonský, M.; Zikán, V.; Kakáč, B.; Jelínek, V. Coll. Czech. Chem. Commun., 1970, 35, 96; Zikán, V.; Vrba, L.; Kakáč, B.; Semonský, M. Coll. Czech. Chem. Commun., 1972, 38, 1091.
20. Semonský, M.; Zikán, V.; Kakáč, B.; Jelínek, V. Coll. Czech. Chem. Commun., 1970, 35, 96; Zikán, V.; Vrba, L.; Kakáč, B.; Semonský, M. Coll. Czech. Chem. Commun., 1972, 38, 1091.
21. Franzén, J.; Kronberg, L. Tetrahedron, 1993, 49, 10945; Meier, J. R. Mutat. Res., 1988, 196, 211; Meier J. R.; DeAngelo, A. B.; Daniel, F. B.; Schenck, K. M.; et al. in Genetic Toxicology of Complex Mixtures; Waters, M. D., Lewtas, J., Moore, M. M., Newnow, S. J., Eds.; Plenum: New York, 1990; p. 185.
22. Franzén, J.; Kronberg, L. Tetrahedron, 1993, 49, 10945; Meier, J. R. Mutat. Res., 1988, 196, 211; Meier J. R.; DeAngelo, A. B.; Daniel, F. B.; Schenck, K. M.; et al. in Genetic Toxicology of Complex Mixtures; Waters, M. D., Lewtas, J., Moore, M. M., Newnow, S. J., Eds.; Plenum: New York, 1990; p. 185.
23. Franzén, J.; Kronberg, L. Tetrahedron, 1993, 49, 10945; Meier, J. R. Mutat. Res., 1988, 196, 211; Meier J. R.; DeAngelo, A. B.; Daniel, F. B.; Schenck, K. M.; et al. in Genetic Toxicology of Complex Mixtures; Waters, M. D., Lewtas, J., Moore, M. M., Newnow, S. J., Eds.; Plenum: New York, 1990; p. 185.
24. Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996; Welch, J. T. Tetrahedron, 1987, 43, 3123 (Tetrah. Rep. No. 221).
25. Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996; Welch, J. T. Tetrahedron, 1987, 43, 3123 (Tetrah. Rep. No. 221).
26. Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds.; Organo-fluorine Compounds in Medicinal Chemistry and Biomedical Applications; Elsevier: Amsterdam, 1993; Banks, R. E., Lowe, K. C., Eds.; Fluorine in Medicine in the 21st Century (Conference Papers); UMIST: Manchester, 1994.
27. Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds.; Organo-fluorine Compounds in Medicinal Chemistry and Biomedical Applications; Elsevier: Amsterdam, 1993; Banks, R. E., Lowe, K. C., Eds.; Fluorine in Medicine in the 21st Century (Conference Papers); UMIST: Manchester, 1994.
28. Ge, P.; Kirk, K. J. Fluorine Chem., 1997, 84, 45; Ge, P.; Kirk, K. J. Org. Chem., 1997, 62, 3340.
29. Ge, P.; Kirk, K. J. Fluorine Chem., 1997, 84, 45; Ge, P.; Kirk, K. J. Org. Chem., 1997, 62, 3340.
30. Komatsu Y., Kitazume T. J. Fluorine Chem. 87:1998;101.
31. Ducher S., Michet A. Bull. Soc. Chim. Fr. 1976;1923-1928.
32. Fischbein P.L., Moore H.W. Org. Synth. 69:1990;205-209.
33. Rappoport, Z. Rec. Trav. Chim. Pays-Bas, 1986, 104, 309; Modena, G. Acc. Chem. Res., 1971, 4, 73; Rappoport, Z. Acc. Chem. Res., 1981, 14, 7.
34. Rappoport, Z. Rec. Trav. Chim. Pays-Bas, 1986, 104, 309; Modena, G. Acc. Chem. Res., 1971, 4, 73; Rappoport, Z. Acc. Chem. Res., 1981, 14, 7.
35. Rappoport, Z. Rec. Trav. Chim. Pays-Bas, 1986, 104, 309; Modena, G. Acc. Chem. Res., 1971, 4, 73; Rappoport, Z. Acc. Chem. Res., 1981, 14, 7.
36. Baasner, B.; Hagemann, H.; Tatlow, J. C., Eds.; Houben-Weyl (Methods of Organic Chemistry): Organo-Fluorine Compounds, Vol. E 10b, Part 2; G. Thieme: Stuttgart, 2000; Hudlický, M., Pavlath, A. E., Eds.; Chemistry of Organic Fluorine Compounds II; ACS Monograph 187: Washington, 1995; Hudlický, M. Chemistry of Organic Fluorine Compounds, 2nd ed., E. Horwood: Chichester, 1992.
37. Baasner, B.; Hagemann, H.; Tatlow, J. C., Eds.; Houben-Weyl (Methods of Organic Chemistry): Organo-Fluorine Compounds, Vol. E 10b, Part 2; G. Thieme: Stuttgart, 2000; Hudlický, M., Pavlath, A. E., Eds.; Chemistry of Organic Fluorine Compounds II; ACS Monograph 187: Washington, 1995; Hudlický, M. Chemistry of Organic Fluorine Compounds, 2nd ed., E. Horwood: Chichester, 1992.
38. Baasner, B.; Hagemann, H.; Tatlow, J. C., Eds.; Houben-Weyl (Methods of Organic Chemistry): Organo-Fluorine Compounds, Vol. E 10b, Part 2; G. Thieme: Stuttgart, 2000; Hudlický, M., Pavlath, A. E., Eds.; Chemistry of Organic Fluorine Compounds II; ACS Monograph 187: Washington, 1995; Hudlický, M. Chemistry of Organic Fluorine Compounds, 2nd ed., E. Horwood: Chichester, 1992.
39. Chambers, R. D., Ed.; Organofluorine Chemistry: Fluorinated Alkenes and Reactive Intermediates (Topics in Current Chemistry, Vol. 192); Springer: Berlin, 1997. Chambers, R. D., Ed.; Organofluorine Chemistry: Techniques and Synthons (Topics in Current Chemistry, Vol. 193); Springer: Berlin, 1997. Chambers, R. D. Fluorine in Organic Chemistry; Durham University: Durham, 1973; p 104.
40. Chambers, R. D., Ed.; Organofluorine Chemistry: Fluorinated Alkenes and Reactive Intermediates (Topics in Current Chemistry, Vol. 192); Springer: Berlin, 1997. Chambers, R. D., Ed.; Organofluorine Chemistry: Techniques and Synthons (Topics in Current Chemistry, Vol. 193); Springer: Berlin, 1997. Chambers, R. D. Fluorine in Organic Chemistry; Durham University: Durham, 1973; p 104.
41. Chambers, R. D., Ed.; Organofluorine Chemistry: Fluorinated Alkenes and Reactive Intermediates (Topics in Current Chemistry, Vol. 192); Springer: Berlin, 1997. Chambers, R. D., Ed.; Organofluorine Chemistry: Techniques and Synthons (Topics in Current Chemistry, Vol. 193); Springer: Berlin, 1997. Chambers, R. D. Fluorine in Organic Chemistry; Durham University: Durham, 1973; p 104.
42. Jeong H., Min Y.K., Park N.K., Cho K.Y., Kim B.T. Bull. Korean Chem. Soc. 15:1994;1031.
43. Nguyen, T.; Wakselman, C. J. Fluorine Chem., 1995, 74, 273; Wessolowski, H.; Gard, G. L.; Röschenthaler, G.-V. J. Fluorine Chem., 1996, 80, 149.
44. Nguyen, T.; Wakselman, C. J. Fluorine Chem., 1995, 74, 273; Wessolowski, H.; Gard, G. L.; Röschenthaler, G.-V. J. Fluorine Chem., 1996, 80, 149.
45. Paleta O., Koňárek J. Collect. Czech. Chem. Commun. 38:1973;66.
46. Paleta, O.; Okrouhlík, J.; Kubelka, V. Collect. Czech. Chem. Commun., 1974, 39, 1336; Svoboda, J.; Paleta, O.; Liška, F.; Dědek, V. Collect. Czech. Chem. Commun., 1981, 46, 1389.
47. Paleta, O.; Okrouhlík, J.; Kubelka, V. Collect. Czech. Chem. Commun., 1974, 39, 1336; Svoboda, J.; Paleta, O.; Liška, F.; Dědek, V. Collect. Czech. Chem. Commun., 1981, 46, 1389.
48. Paleta O., Pelter A., Kebrle J. Tetrahedron Lett. 35:1994;9259.
49. Pearson, R. G., Ed.; Hard and Soft Acids and Bases; Dowden, Hutchinson & Ross: Stroudsburg, 1973. Ho, T. L. Chem. Rev., 1975, 75, 1. Ho, T. L. Hard and Soft Acids and Bases in Organic Chemistry; Academic Press: New York, 1977.
50. Pearson, R. G., Ed.; Hard and Soft Acids and Bases; Dowden, Hutchinson & Ross: Stroudsburg, 1973. Ho, T. L. Chem. Rev., 1975, 75, 1. Ho, T. L. Hard and Soft Acids and Bases in Organic Chemistry; Academic Press: New York, 1977.
51. Pearson, R. G., Ed.; Hard and Soft Acids and Bases; Dowden, Hutchinson & Ross: Stroudsburg, 1973. Ho, T. L. Chem. Rev., 1975, 75, 1. Ho, T. L. Hard and Soft Acids and Bases in Organic Chemistry; Academic Press: New York, 1977.
52. Kvíčala J., Plocar J., Vlasáková R., Paleta O., Pelter A. Synlett. 1997;986.
53. Paleta, O.; Duda, Z.; Hajduch J.; unpublished results.
54. Bertucco A., Brennan J., Fachini M., Kluge S., Murphy P.J. Tetrahedron. 50:1994;27.
55. Journal F.F., Maestro M.C., Martin M.R., Martin M.V., Sanchez F.J. Chem. Res. Miniprint. 6:1980;2662-2682.
56. Arahori, H.; Sato, N. Jpn. Kokai Tokkyo Koho JP 63,170, 370-371 (1988); Chem. Abs. 1989, 110, 8030. Ohnishi, H.; Iihama, T.; Ishimitsu, K.; Yamada, T. PCT Int. Appl. WO 92 00,964 (1992); Chem. Abs. 1992, 117, 7806.
57. Arahori, H.; Sato, N. Jpn. Kokai Tokkyo Koho JP 63,170, 370-371 (1988); Chem. Abs. 1989, 110, 8030. Ohnishi, H.; Iihama, T.; Ishimitsu, K.; Yamada, T. PCT Int. Appl. WO 92 00,964 (1992); Chem. Abs. 1992, 117, 7806.
58. Arahori, H.; Sato, N. Jpn. Kokai Tokkyo Koho JP 63,170, 370-371 (1988); Chem. Abs. 1989, 110, 8030. Ohnishi, H.; Iihama, T.; Ishimitsu, K.; Yamada, T. PCT Int. Appl. WO 92 00,964 (1992); Chem. Abs. 1992, 117, 7806.
59. Arahori, H.; Sato, N. Jpn. Kokai Tokkyo Koho JP 63,170, 370-371 (1988); Chem. Abs. 1989, 110, 8030. Ohnishi, H.; Iihama, T.; Ishimitsu, K.; Yamada, T. PCT Int. Appl. WO 92 00,964 (1992); Chem. Abs. 1992, 117, 7806.
60. Beak P., Basu A., Gallagher D.J., Park Y.S., Thayumanavan S. Acc. Chem. Res. 29:1996;552.
61. Sterlin, S. R.; Yatsenko, R. D.; Knunyants, I. L. Khim. Nauka Promy., 1958, 3, 540; Chem. Abs., 1959, 53, 4959.
62. Sterlin, S. R.; Yatsenko, R. D.; Knunyants, I. L. Khim. Nauka Promy., 1958, 3, 540; Chem. Abs., 1959, 53, 4959.
63. Tarrant P., Johncock P., Savory J. J. Org. Chem. 28:1963;839.
64. Normant J.F., Foulon J.P., Masure D., Sauvetre R., Villieras J. Synthesis. 1975;122.
65. Nguyen T., Wakselman C. J. Org. Chem. 54:1989;5640.
66. Furniss B.S., Hammford A.J., Smith P.W.G., Tatchell A.R. Vogel's Textbook of Practical Organic Chemistry. (5th ed.) :1991;J. Wiley, New York. Ch. 4.
67. House H.O., Chu Ch., Wilkins J.M., Umen M.J. J. Org. Chem. 40:1975;1460.
68. Šendrik V.P., Paleta O., Dědek V. Collect. Czech. Chem. Commun. 42:1977;2530.
69. Paleta O.; Duda Z.; Holý A.; in preparation.