Synthetic studies on bioactive natural products utilizing the elimination reaction of 1,2-dibromides possessing oxygen-functional groups at adjacent positions

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 66, Issue 2, 2008, Pages 139-147

  Ohgiya, Tadaaki ^a   Kutsumura, Noriki ^a   Nishiyama, Shigeru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

2 bromol 1 alkene; Alkyne; Muricatacin; Propargyl ether; Regioselective elimination; Sapinofuranone B; Tanikolide; Tremetone; Tuliparin B

Indexed keywords

ETHERS; FUNCTIONAL GROUPS; HYDROGEN; OLEFINS; REACTION KINETICS;

DIBROMOALKANES; RADICAL REACTIONS; VINYL LITHIUMS;

BIOMATERIALS;

EID: 42649089194     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.66.139     Document Type: Article

References (53)

1. (a) L. A. Paquette, J. E. Hofferberth, J. Org. Chem., 68, 2266 (2003);
2. (b) C. S. Poss, S. D. Rychnovsky, S. L. Schreiber, J. Ann. Chem. Soc., 115, 3360 (1993)
3. P. Knochel, S. A. Rao, J. Am. Chem. Soc., 112, 6146 (1990)
4. (a) N. Miyaura, A. Suzuki, Chem. Rev., 95, 2457 (1995);
5. (b) P. Pinho, A. J. Minnaard, B. L. Feringa, Org. Lett., 5, 259 (2003);
6. (c) E. Negishi, L. F. Valente, M. Kobayashi, J. Am. Chem. Soc., 102, 3298 (1980);
7. (d) J. Uenishi, M. Ohmi, Heterocycles, 61, 365 (2003);
8. M. F. Semmelhack, S. J. Brickner, J. Org. Chem., 46, 1723 (1981)
9. M. Yokota, M. Toyota, M. Ihara, Chem. Common., 2003, 422
10. M. P. VanBrunt, R. O. Ambenge, S. M. Weinreh, J. Org. Chenn, 68, 3323 (2003)
11. (a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett., 16, 4467 (1975);
12. (b) I. Izzo, S. De Caro, F. De Riccardis, A. Spinella, ibid., 41, 3975 (2000);
13. (c) R. E. Ireland, P. Wipf, J. Org. Chem., 55, 1425 (1990)
14. T. Ohgiya, S. Nishiyama, Chem. Lett., 33, 1084 (2004)
15. (a) N. Kutsumura, T. Yokoyama, T. Ohgiya, S. Nishiyama, Tetrahedron Lett., 47, 4133 (2006);
16. (b) T. Yokoyama, N. Kutsumura, T. Ohgiya, S. Nishiyama, Bull. Chem. Soc. Jpn., 80, 578 (2007)
17. (a) S. Hara, H. Dojo, S. Takinami, A. Suzuki, Tetrahedron Lett., 24, 731 (1983);
18. (b) J. D. White, P. R. Blakemore, C. C. Browder, J. Hong, C. M. Lincoln, P. A. Nagornyy, L. A. Robarge, D. J. Wardrop, J. Am. Chem. Soc., 123, 8593 (2001)
19. (a) R. K. Boeckman, Jr., D. M. Blum, J. Org. Chem., 39, 3307 (1974);
20. (b) J. Cousseau, Synthesis, 1980, 805
21. W. A. Bonner, J. I. De Graw, Jr., D. M. Bowen, V. R. Shah, Tetrahedron Lett., 2, 417 (1961)
22. (a) S. Valverde Lopez, B. Rodriguez Gonzalez, An. Quint., 67, 879 (1971);
23. (b) A. Sala, M. C. Recio, G. R. Schinella, S. Manez, R. M. Giver, J.-L. Rios, Ear. J. Pharmacol., 460, 219 (2003);
24. (c) A. Sala, M. C. Recio, R. M. Giner, S. Manez, J.-L. Rios, J. Not. Prod., 64, 1360 (2001);
25. (d) G. G. Zapesochnaya, T. V. Dzyadevich, B. S. Karasartov, Khirn. Prir. Soedin., 1990, 409;
26. (e) P. Pritschow, J. Jakupovic, F. Bohlmann, M. Bittner, H. M. Niemeyer, Phylochem., 30, 893 (1991);
27. (f) F. Bohlmann, C. Scheidges, C. Zdero, R. M. King, H. Robinson, ibid., 23, 1109 (1984);
28. (g) J. Ito, F.-R. Chang, H.-K. Wang, Y. K. Park, M. Ikegaki, N. Kilgore, K.-H. Lee, J. Nat. Prod., 64, 1278 (2001);
29. (h) T. J. Schmidt, M. R. Hildebrand, G. Willuhn, Planta Med., 69, 258 (2003)
30. T. Ohgiya, S. Nishiyama, Heterocycles, 63, 2349 (2004)
31. (a) R. Tschesche, F.-J. Kammerer, G. Wulff, F. Schonbeck, Tetrahedron Lett., 9, 701 (1968);
32. (b) R. Tschesche, F.-J. Kammerer, G. Wulff, Chem. Ber., 102, 2057 (1969)
33. L. P. Christensen, Phytochem., 51, 969 (1999)
34. B. H. H. Bergman, Neth. J. Pl. Path., 72, 222 (1966)
35. F. Schonbeck, C. Schroeder, Physiol. Plant Pathol., 2, 91 (1972)
36. (a) A. Lammimaa, T. Estlander, R. Jolanki, L. Kanerva, Contact Dermatitis, 34, 330 (1996);
37. (b) P. Barbier, C. Benezra, J. Med. Chem., 29, 868 (1986)
38. (a) T. Ohgiya, S. Nishiyama, Tetrahedron Lett., 45, 8273 (2004);
39. (b) T. Ohgiya, K. Nakamura, S. Nishiyama, Bull. Chem. Soc. Jpn., 78, 1549 (2005)
40. I. P. Singh, K. E. Milligan, W. H. Gerwick, J. Nat. Prod., 62, 1333 (1999)
41. J. H. Cardllina II, R. E. Moore, E. V. Arnold, J. Clardy, J. Org. Chem., 44, 4039 (1979)
42. (a) M. G. Finn, K. B. Sharpless, "On the Mechanism of Asymmetric Epoxydation with Titanium-Tartrate Catalysts. Asymmetric Synthesis" ed. by J. D. Morrison, Academic Press, Inc., Tokyo, 1985, Vol. 5, p 247;
43. (b) T. Katsuki, K. B. Sharpless, J. Ann. Cheer. Soc., 102, 5974 (1980)
44. (a) A. Furstner, D. De Souza, L. Parra-Rapado, J. T. Jensen, Angera. Cheer. Int. Ed., 42, 5358 (2003);
45. (b) D. Kim, J. Lee, P. J. Shim, J. I. Lim, T. Doi, S. Kim, J. Org. Chem., 67, 772 (2002);
46. (c) T. Yoshimitsu, K. Ogasawara, J. Cherry. Soc., Cherry. Common., 1994, 2197;
47. (d) P. F. Keusenkothen, M. B. Smith, J. Chem. Soc., Perkin Trans. 1, 1994, 2485
48. M. J. Rieser, J. F. Kozlowski, K. V. Wood, J. L. McLaughlin, Tetrahedron Lett. 32, 1137 (1991)
49. A. Evidente, L. Sparapano, O. Fierro, G. Brunu, A. Motta, J. Nat. Prod., 62, 253 (1999)
50. J. A. Webb, J. E. Klijn, P. Aru Hill, J. L. Bennett, N. S. Goroff, J. Org. Chem., 69, 660 (2004)
51. (a) K. Fujii, K. Maki, M. Kanai, M. Shibasaki, Org. Lett., 5, 733 (2003);
52. (b) D. E. Chavez, E. N. Jacobsen, Angera. Chem. Int. Ed., 40, 3667 (2001);
53. (c) A. G. Myers, B. Zheng, M. Movassaghi, J. Org. Chem., 62, 7507 (1997)