Synthesis and domino metathesis of functionalized 7-oxanorbornene analogs toward cis-fused heterocycles

Tetrahedron

Volumn 64, Issue 12, 2008, Pages 2740-2749

  Ikoma, Minoru ^a   Oikawa, Masato ^a   Sasaki, Makoto ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

7 Oxanorbornene; Cis fused heterocycle; Diels Alder reaction; Domino metathesis

Indexed keywords

3 IODOACRYLAMIDE; 7 OXANORBORNENE ANALOG; ACRYLAMIDE DERIVATIVE; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS;

ALNUS;

EID: 39149118885     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.067     Document Type: Article

References (61)

1. Yasumoto T. Chem. Rec. 1 (2001) 228
2. Yasumoto T. Proc. Jpn. Acad. Ser. B, Phys. Biol. Sci. 81 (2005) 43
3. Nakata T. Chem. Rev. 105 (2005) 4314
4. Inoue M. Chem. Rev. 105 (2005) 4379
5. Clark J.S. Chem. Commun. (2006) 3571
6. Sakai R., Kamiya H., Murata M., and Shimamoto K. J. Am. Chem. Soc. 119 (1997) 4112
7. Sakai R., Koike T., Sasaki M., Shimamoto K., Oiwa C., Yano A., Suzuki K., Tachibana K., and Kamiya H. Org. Lett. 3 (2001) 1479
8. Haneishi T., Terahara A., Kayamori H., Yabe J., and Arai M. J. Antibiot. 29 (1976) 870
9. Murata M., Naoki H., Matsunaga S., Satake M., and Yasumoto T. J. Am. Chem. Soc. 116 (1994) 7098
10. Brown M.J., Harrison T., and Overman L.E. J. Am. Chem. Soc. 113 (1991) 5378
11. Sasaki M., Maruyama T., Sakai R., and Tachibana K. Tetrahedron Lett. 40 (1999) 3195
12. Sasaki M., Koike T., Sakai R., and Tachibana K. Tetrahedron Lett. 41 (2000) 3923
13. Shoji M., Shiohara K., Oikawa M., Sakai R., and Sasaki M. Tetrahedron Lett. 46 (2005) 5559
14. Takahashi K., Matsumura T., Ishihara J., and Hatakeyama S. Chem. Commun. (2007) 4158
15. Zheng W.J., DeMattei J.A., Wu J.P., Duan J.J.W., Cook L.R., Oinuma H., and Kishi Y. J. Am. Chem. Soc. 118 (1996) 7946
16. Miyata O., Iba R., Hashimoto J., and Naito T. Org. Biomol. Chem. 1 (2003) 772
17. Snider B.B., and Hawryluk N.A. Org. Lett. 2 (2000) 635
18. Phillips D., and Chamberlin A.R. J. Org. Chem. 67 (2002) 3194
19. Naito T., Nair J.S., Nishiki A., Yamashita K., and Kiguchi T. Heterocycles 53 (2000) 2611
20. Torikai K., Yari H., Murata M., and Oishi T. Heterocycles 70 (2006) 161
21. Hayashi N., Fujiwara K., and Murai A. Tetrahedron Lett. 37 (1996) 6173
22. Lygo B., Slack D., and Wilson C. Tetrahedron Lett. 46 (2005) 6629
23. Schreiber S.L. Science 287 (2000) 1964
24. Burke M.D., and Schreiber S.L. Angew. Chem., Int. Ed. 43 (2004) 46
25. For our related study, see Refs. 32 and 41.
26. Holub N., and Blechert S. Chem. Asian J. 2 (2007) 1064
27. Arjona O., Csaky A.G., Murcia M.C., and Plumet J. Tetrahedron Lett. 41 (2000) 9777
28. Ranu B.C., and Hajra A. J. Chem. Soc., Perkin Trans. 1 (2001) 2262
29. Vogel P., Fattori D., Gasparini F., and Ledrian C. Synlett (1990) 173
30. Kappe C.O., Murphree S.S., and Padwa A. Tetrahedron 53 (1997) 14179
31. Hayashi Y., Nakamura M., Nakao S., Inoue T., and Shoji M. Angew. Chem., Int. Ed. 41 (2002) 4079
32. Rhodes C.N., and Brown D.R. J. Chem. Soc., Faraday Trans. 89 (1993) 1387
33. Fraile J.M., Garcia J.I., Massam J., Mayoral J.A., and Pires E. J. Mol. Catal. A 123 (1997) 43
34. Vieira E., and Vogel P. Helv. Chim. Acta 66 (1983) 1865
35. Black K.A., and Vogel P. Helv. Chim. Acta 67 (1984) 1612
36. Jung M.E. Synlett (1990) 186
37. Takeuchi R., Tanabe K., and Tanaka S. J. Org. Chem. 65 (2000) 1558
38. Diels-Alder reaction of cis-3-chloroacrylic acid derivative has been reported and summarized in the following, see:. Pohland A.E., and Benson W.R. Chem. Rev. 66 (1966) 161
39. Gao Z.G., Kim S.K., Biadatti T., Chen W.Z., Lee K., Barak D., Kim S.G., Johnson C.R., and Jacobson K.A. J. Med. Chem. 45 (2002) 4471
40. Linz G., Weetman J., Abdelhady A.F., and Helmchen G. Tetrahedron Lett. 30 (1989) 5599
41. Griffith W.P., Ley S.V., Whitcombe G.P., and White A.D. J. Chem. Soc., Chem. Commun. (1987) 1625
42. 41 Application of this method for the butenyl analog is under investigation.
43. For a review, see:. Arjona O., Csaky A.G., and Plumet J. Eur. J. Org. Chem. (2003) 611
44. Oikawa M., Ikoma M., and Sasaki M. Tetrahedron Lett. 46 (2005) 5863
45. Lee D.S., Sello J.K., and Schreiber S.L. Org. Lett. 2 (2000) 709
46. Sello J.K., Andreana P.R., Lee D.S., and Schreiber S.L. Org. Lett. 5 (2003) 4125
47. Garber S.B., Kingsbury J.S., Gray B.L., and Hoveyda A.H. J. Am. Chem. Soc. 122 (2000) 8168
48. Hoveyda A.H., Gillingham D.G., Van Veldhuizen J.J., Kataoka O., Garber S.B., Kingsbury J.S., and Harrity J.P.A. Org. Biomol. Chem. 2 (2004) 8
49. Scholl M., Ding S., Lee C.W., and Grubbs R.H. Org. Lett. 1 (1999) 953
50. Connon S.J., and Blechert S. Angew. Chem., Int. Ed. 42 (2003) 1900
51. Miller S.J., Kim S.H., Chen Z.R., and Grubbs R.H. J. Am. Chem. Soc. 117 (1995) 2108
52. Furstner A., and Langemann K. J. Org. Chem. 61 (1996) 8746
53. Stragies R., and Blechert S. Synlett (1998) 169
54. Herisson J.L., and Chauvin Y. Makromol. Chem. 141 (1971) 161
55. Mayo P., and Tam W. Tetrahedron 58 (2002) 9513
56. Ikoma, M.; Oikawa, M.; Sakai, R.; Shimamoto, K.; Sasaki, M. J. Comb. Chem., in press.
57. Weeresakare G.M., Liu Z.Q., and Rainier J.D. Org. Lett. 6 (2004) 1625
58. Liu Z.Q., and Rainier J.D. Org. Lett. 7 (2005) 131
59. Bogevig A., Juhl K., Kumaragurubaran N., Zhuang W., and Jorgensen K.A. Angew. Chem., Int. Ed. 41 (2002) 1790
60. The usefulness of the present synthetic pathway has been demonstrated in our recent development of glutamate analogs with interesting biological activity, see Ref. 41.
61. Shoji M., Akiyama N., Tsubone K., Lash L.L., Sanders J.M., Swanson G.T., Sakai R., Shimamoto K., Oikawa M., and Sasaki M. J. Org. Chem. 71 (2006) 5208