A new route to γ-arylidenebutyrolactones via a tandem carbopalladation-heterocyclisation sequence: A formal synthesis of U-68,215

Tetrahedron

Volumn 52, Issue 35, 1996, Pages 11463-11478

  Cavicchioli, Marcello ^a   Decortiat, Sylvie ^a   Bouyssi, Didier ^a   Goré, Jacques ^a   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

15 CYCLOHEXYL 15 HYDROXY 2',9ALPHA METHANO 4,5,6,16,17,18,19,20 OCTANOR 3 OXA 3,7 (1,3 INTERPHENYLENE)PROSTANOIC ACID; ANTIULCER AGENT; GAMMA BUTYROLACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030603103     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00637-0     Document Type: Article

References (47)

1. 1. (a) Fournet, G. ; Balme, G. ; Gore, J. ; Tetrahedron Lett., 1989, 30, 69-70.
2. (b) Bouyssi, D. ; Balme, G. ; Fournet, G. ; Monteiro, N. ; Gore, J. ; Tetrahedron Lett., 1991, 3, 1641-1644. This new palladium catalyzed cyclisation was first observed on alkylidene cyclopropanes see : Fournet, G. ; Balme, G. ; Gore, J. ; Tetrahedron Lett., 1987, 28, 4533-36 and Tetrahedron, 1988, 44, 5809-5821.
3. (b) Bouyssi, D. ; Balme, G. ; Fournet, G. ; Monteiro, N. ; Gore, J. ; Tetrahedron Lett., 1991, 3, 1641-1644. This new palladium catalyzed cyclisation was first observed on alkylidene cyclopropanes see : Fournet, G. ; Balme, G. ; Gore, J. ; Tetrahedron Lett., 1987, 28, 4533-36 and Tetrahedron, 1988, 44, 5809-5821.
4. (b) Bouyssi, D. ; Balme, G. ; Fournet, G. ; Monteiro, N. ; Gore, J. ; Tetrahedron Lett., 1991, 3, 1641-1644. This new palladium catalyzed cyclisation was first observed on alkylidene cyclopropanes see : Fournet, G. ; Balme, G. ; Gore, J. ; Tetrahedron Lett., 1987, 28, 4533-36 and Tetrahedron, 1988, 44, 5809-5821.
5. 2. Balme, G. ; Bouyssi, D.; Tetrahedron, 1994, 50, 403-414.
6. 3. (a) Fournet, G. ; Balme, G. ; Vanhemelryck, B. ; Gore, J. ; Tetrahedron Lett., 1990, 31, 5147-5150.
7. (b) Fournet, G. ; Balme, G. ; Gore, J. ; Tetrahedron, 1991, 47, 6293-6304.
8. (c) Bouyssi, D. ; Goré, J. ; Balme , G. ; Tetrahedron Lett. 1991, 32, 6541-6544.
9. 4. Luo, F.T. ; Schreuder, I. ; Wang, R.J. ; J.Org.Chem., 1992, 57, 2213-2215.
10. 5. Luo, F.T. ; Wang, R.T. ; Tetrahedron Lett., 1992, 33, 6835-6838.
11. 6 Bouyssi, D. ; Goré, J. ; Balme, G. ; Tetrahedron Lett. 1992, 33, 2811-2814.
12. 7. Bouyssi, D. ; Goré, J. ; Balme, G. ; Louis D. ; Wallach, J. Tetrahedron Lett. 1993, 34, 3129-3130.
13. 8. Arcadi, A. ; Burini, A. ; Cacchi, S. ; Delmastro, M. ; Marinelli, F. ; Pietroni, B.R. J. Org. Chem. 1992, 57, 976-982.
14. 9. Preliminary accounts of the work have been published: Cavicchioli, M. ; Bouyssi, D. ; Goré, J. ; Balme, G. ; Tetrahedron Lett. 1996, 37, 1429-1432, and the details of the studies are presented in this paper.
15. 10. Review: Becker, K.B. Tetrahedron 1980, 36, 1717-1745.
16. 11. For examples of the utilisation of KF as base, see: Ferroud, D. ; Genet, J.P. ; S. Grisoni. ;Tetrahedron Lett. 1984, 25, 4379-4382. Genet, J.P. ; Grisoni, S. ; Tetrahedron Lett. 1986, 27, 4165-4168. Genet, J.P. ; Grisoni, S. ;Tetrahedron Lett. 1988, 29, 4543-4546. Ostaszynski, A. ; Wielgat, J. ;Urbanski, T.; Tetrahedron 1966, 25, 1929-1938.
17. 11. For examples of the utilisation of KF as base, see: Ferroud, D. ; Genet, J.P. ; S. Grisoni. ;Tetrahedron Lett. 1984, 25, 4379-4382. Genet, J.P. ; Grisoni, S. ; Tetrahedron Lett. 1986, 27, 4165-4168. Genet, J.P. ; Grisoni, S. ;Tetrahedron Lett. 1988, 29, 4543-4546. Ostaszynski, A. ; Wielgat, J. ;Urbanski, T.; Tetrahedron 1966, 25, 1929-1938.
18. 11. For examples of the utilisation of KF as base, see: Ferroud, D. ; Genet, J.P. ; S. Grisoni. ;Tetrahedron Lett. 1984, 25, 4379-4382. Genet, J.P. ; Grisoni, S. ; Tetrahedron Lett. 1986, 27, 4165-4168. Genet, J.P. ; Grisoni, S. ;Tetrahedron Lett. 1988, 29, 4543-4546. Ostaszynski, A. ; Wielgat, J. ;Urbanski, T.; Tetrahedron 1966, 25, 1929-1938.
19. 11. For examples of the utilisation of KF as base, see: Ferroud, D. ; Genet, J.P. ; S. Grisoni. ;Tetrahedron Lett. 1984, 25, 4379-4382. Genet, J.P. ; Grisoni, S. ; Tetrahedron Lett. 1986, 27, 4165-4168. Genet, J.P. ; Grisoni, S. ;Tetrahedron Lett. 1988, 29, 4543-4546. Ostaszynski, A. ; Wielgat, J. ;Urbanski, T.; Tetrahedron 1966, 25, 1929-1938.
20. 12. Jeffery, T. Tetrahedron Lett. 1991, 32, 2121-2124.
21. 13. Vittoz, P.; Bouyssi, D., Traversa, C., Goré, J., Balme, G. Tetrahedron Lett. 1994, 35, 1871-1874.
22. 14. (a) Castaner, B.J. ; Pascual, J. J. Chem. Soc. 1958, 3962-3964.
23. (b) Spencer, R.W. ; Tam, T.F. ; Thomas, E. ; Robinson, V.J. ; Krantz A. J. Am. Chem. Soc. 1986, 108, 5589-5597;
24. 15. Watanabe, M.; Morimoto, H.; Furukawa, S. Heterocycles, 1993, 36, 2681-2686. Kelly, T.R. ; Ohashi, N.; Armstrong-Chan, R.J. ; Bell, S.H. J. Am. Chem. Soc. 1986, 108, 7100-7101. Kelly, T.R. ; Bell, S.H. ; Ohashi, N.; Amstrong-Chan, R.J. J. Am. Chem. Soc. 1988, 110, 6471-6472.
25. 15. Watanabe, M.; Morimoto, H.; Furukawa, S. Heterocycles, 1993, 36, 2681-2686. Kelly, T.R. ; Ohashi, N.; Armstrong-Chan, R.J. ; Bell, S.H. J. Am. Chem. Soc. 1986, 108, 7100-7101. Kelly, T.R. ; Bell, S.H. ; Ohashi, N.; Amstrong-Chan, R.J. J. Am. Chem. Soc. 1988, 110, 6471-6472.
26. 15. Watanabe, M.; Morimoto, H.; Furukawa, S. Heterocycles, 1993, 36, 2681-2686. Kelly, T.R. ; Ohashi, N.; Armstrong-Chan, R.J. ; Bell, S.H. J. Am. Chem. Soc. 1986, 108, 7100-7101. Kelly, T.R. ; Bell, S.H. ; Ohashi, N.; Amstrong-Chan, R.J. J. Am. Chem. Soc. 1988, 110, 6471-6472.
27. 16. Isolation and biological properties, see: Pandey, R.C. ; Toussaint, M.W.;Strohane, R.M. ; Kalita, C.C. ; Aszalos, A.A. ; Garretson, A.L. ; Wei, T.T.; Byrne, K.W. ; Geoghegan, R.F. ; Jr.; White, R.j ; J. Antibiot. 1981, 34, 1389. Warnick-Pickle, D.J. ; Byrne, K.W. ; Pandey, R.C. ; White, R.J. ; J. Antibiot., 1981, 34, 402. Misra, R.; Pandey, R.C. ; Silverton, J.V. ; J. Am. Chem. Soc. 1982, 104, 4478-4479. Misra, R. ; Pandey, R.C. ; Hilton, B.D. ; Roller, P.P. ; Silverton, J.V. ; J. Antibiot. 1987, 40, 786.
28. 16. Isolation and biological properties, see: Pandey, R.C. ; Toussaint, M.W.;Strohane, R.M. ; Kalita, C.C. ; Aszalos, A.A. ; Garretson, A.L. ; Wei, T.T.; Byrne, K.W. ; Geoghegan, R.F. ; Jr.; White, R.j ; J. Antibiot. 1981, 34, 1389. Warnick-Pickle, D.J. ; Byrne, K.W. ; Pandey, R.C. ; White, R.J. ; J. Antibiot., 1981, 34, 402. Misra, R.; Pandey, R.C. ; Silverton, J.V. ; J. Am. Chem. Soc. 1982, 104, 4478-4479. Misra, R. ; Pandey, R.C. ; Hilton, B.D. ; Roller, P.P. ; Silverton, J.V. ; J. Antibiot. 1987, 40, 786.
29. 16. Isolation and biological properties, see: Pandey, R.C. ; Toussaint, M.W.;Strohane, R.M. ; Kalita, C.C. ; Aszalos, A.A. ; Garretson, A.L. ; Wei, T.T.; Byrne, K.W. ; Geoghegan, R.F. ; Jr.; White, R.j ; J. Antibiot. 1981, 34, 1389. Warnick-Pickle, D.J. ; Byrne, K.W. ; Pandey, R.C. ; White, R.J. ; J. Antibiot., 1981, 34, 402. Misra, R.; Pandey, R.C. ; Silverton, J.V. ; J. Am. Chem. Soc. 1982, 104, 4478-4479. Misra, R. ; Pandey, R.C. ; Hilton, B.D. ; Roller, P.P. ; Silverton, J.V. ; J. Antibiot. 1987, 40, 786.
30. 16. Isolation and biological properties, see: Pandey, R.C. ; Toussaint, M.W.;Strohane, R.M. ; Kalita, C.C. ; Aszalos, A.A. ; Garretson, A.L. ; Wei, T.T.; Byrne, K.W. ; Geoghegan, R.F. ; Jr.; White, R.j ; J. Antibiot. 1981, 34, 1389. Warnick-Pickle, D.J. ; Byrne, K.W. ; Pandey, R.C. ; White, R.J. ; J. Antibiot., 1981, 34, 402. Misra, R.; Pandey, R.C. ; Silverton, J.V. ; J. Am. Chem. Soc. 1982, 104, 4478-4479. Misra, R. ; Pandey, R.C. ; Hilton, B.D. ; Roller, P.P. ; Silverton, J.V. ; J. Antibiot. 1987, 40, 786.
31. 17. The application of this reaction to the synthesis of the BCDE ring part of Fredericamycin A is in progress.
32. 18. Rajamannar, T. ; Balasubramanian, K. Tetrahedron Lett. 1988, 29, 5789-5792.
33. 19. Canonne, P. ; Boulanger, R. ; Angers, P. Tetrahedron Lett. 1991, 32, 5861-5864.
34. 20. Ma, S. ; Lu, X. ; Li, Z. ; J. Org. Chem. 1992, 57 , 709-713.
35. 21. (a) Izumi, T.; Kasahara, A. ; Bull. Chem. Soc. Jpn. 1975, 48, 1673.
36. (b) Tamaru, Y. ; Higashimura, H. ; Naka, K. ; Hojo, M.; Yoshida, Z ; Angew. Chem., int. Ed. Engl. 1977, 24, 1045.
37. (c) Korte, D.E. ; Hegedus, L.S. ; Wirth, R.K. ; J. Org. Chem. 1977, 42, 1329.
38. (d) Backvall, J.-E. ; Anderssan, P. G. ; Vagberg. J.O.Tetrahedron Lett. 1989, 30, 137-140.
39. (e) Kasahara, A. ; Izumi, T. ; Sato, K. ; Maemura, M. ; Hayasaka, T. Bull. Chem. Soc. Jpn. 1977, 50, 1899.
40. (f) Larock, R.C. ; Hightower, T.R. ; J. Org. Chem. 1993, 58, 5298-5300.
41. 22. To our knowledge, there are only examples of intramolecular nucleophilic attack of carbon nucleophiles on a double bond activated by an organopalladium species; see: ref 1 and 2
42. 23. a) Aristoff, P.A. ; Jonhson, P.D. ; Harrison, A.W. J. Am. Chem. Soc. 1985, 107, 7967-7974.
43. b) see also: Wu, G. Shimoyama, I. ; Negishi, E. ; J. Org. Chem. 1991, 56, 6505-6506.
44. 24. Leed, A.R. ; Boettger, D.S. ; Ganem, B. J. Org. Chem. 1980, 45, 1098-1106.
45. 25. Lounasmaa, M. ; Acta. Chem. Scand., 1968, 22, 2388-2390.
46. 26. For preparation of 4a, see: Organic Syntheses, James D. White, Editor, Volume 68 , 182-187.
47. 27. Neghishi, E-I. ; Copéret, C. Sugihara, T. ; Shimoyama, I. ; Zhang, Y. ; Wu, G. ; Tour, J. ; Tetrahedron 1994, 50, 425-436.