Synthesis of oxacyclic dienes via ring-closing enyne metathesis: Difference in construction of eight-membered rings

Tetrahedron Letters

Volumn 53, Issue 26, 2012, Pages 3389-3392

  Zhang, Lin Lin ^a   Zhang, Wen Zhen ^a   Ren, Xiang ^a   Tan, Xin Yan ^a   Lu, Xiao Bing ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Eight membered ring; Enyne metathesis; Grubbs' catalyst; Oxacyclic dienes

Indexed keywords

ALKADIENE; ALKYNE; HETEROCYCLIC NITRO COMPOUND; METHYL GROUP; OXYGEN;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CONTROLLED STUDY; GRUBBS CATALYST; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 84861527940     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.04.107     Document Type: Article

References (69)

1. T.M. Trnak, and R.H. Grubbs Acc. Chem. Res. 34 2001 18
2. R.H. Grubbs Tetrahedron 60 2004 7117
3. D. Astruc New J. Chem. 29 2005 42
4. P. Schwab, R.H. Grubbs, and J.W. Ziller J. Am. Chem. Soc. 118 1996 100
5. M. Scholl, S. Ding, C.W. Lee, and R.H. Grubbs Org. Lett. 1 1999 953
6. M.S. Sanford, J.A. Love, and R.H. Grubbs J. Am. Chem. Soc. 123 2001 6543
7. T.M. Trnka, J.P. Morgan, M.S. Sanford, T.E. Wilhelm, M. Scholl, T.-L. Choi, S. Ding, M.W. Day, and R.H. Grubbs J. Am. Chem. Soc. 125 2003 2546
8. S.T. Diver, and A.J. Giessert Chem. Rev. 104 2004 1317
9. E.C. Hansen, and D. Lee Acc. Chem. Res. 39 2006 509
10. M. Mori Adv. Synth. Catal. 349 2007 121
11. S.T. Diver Coord. Chem. Rev. 251 2007 671
12. M. Mori Materials 3 2010 2087
13. C. Fischmeister, and C. Beilstein Bruneau J. Org. Chem. 7 2011 156
14. A. Kinoshita, N. Sakakibara, and M. Mori J. Am. Chem. Soc. 119 1997 12388
15. R. Stragies, M. Schuster, and S. Blechert Angew. Chem., Int. Ed. 36 1997 2518
16. J.A. Smulik, and S.T. Diver J. Org. Chem. 65 2000 1788
17. A.A. Kulkarni, and S.T. Diver Org. Lett. 5 2003 3463
18. A.A. Kulkarni, and S.T. Diver J. Am. Chem. Soc. 126 2004 8110
19. S. Park, M. Kim, and D. Lee J. Am. Chem. Soc. 127 2005 9410
20. S.V. Maifeld, and D. Lee Chem. Eur. J. 11 2005 6118
21. H. Villar, M. Frings, and C. Bolm Chem. Soc. Rev. 36 2007 55
22. X. Yang, Y. Zhang, and Z. Shao Chinese J. Org. Chem. 30 2010 968
23. K.C. Majumdar RSC Advances 1 2011 1152
24. A. Kinoshita, and M. Mori Synlett 1994 1020
25. S.-H. Kim, W.J. Zuercher, N.B. Bowden, and R.H. Grubbs J. Org. Chem. 61 1996 1073
26. A. Furstner, L. Ackermann, B. Gabor, R. Goddard, C.W. Lehmann, R. Mynott, F. Stelzer, and O.R. Thiel Chem. Eur. J. 7 2001 3236
27. T. Kitamura, Y. Sato, and M. Mori Adv. Synth. Catal. 344 2002 678
28. H. Guo, R.J. Madhushaw, F.-M. Shen, and R.-S. Liu Tetrahedron 58 2002 5627
29. R. Castarlenas, M. Eckert, and P.H. Dixneuf Angew. Chem., Int. Ed. 44 2005 2576
30. B.G. Kim, and M.L. Snapper J. Am. Chem. Soc. 128 2006 52
31. H. Wakamatsu, Y. Sato, R. Fujita, and M. Mori Adv. Synth. Catal. 349 2007 1231
32. K.C. Nicolaou, P.G. Bulger, and D. Sarlah Angew. Chem., Int. Ed. 44 2005 4490
33. A. Kinoshita, and M. Mori J. Org. Chem. 61 1996 8356
34. J.S. Clark, R.J. Townsend, A.J. Blake, S.J. Teat, and A. Johns Tetrahedron Lett. 42 2001 3235
35. M.E. Layton, C.A. Morales, and M.D. Shair J. Am. Chem. Soc. 124 2002 773
36. R.R. Cesati III, J. de Armas, and A.H. Hoveyda J. Am. Chem. Soc. 126 2004 96
37. T. Kitamura, Y. Sato, and M. Mori Tetrahedron 60 2004 9649
38. J.B. Brenneman, R. Machauer, and S.F. Martin Tetrahedron 60 2004 7301
39. T. Tomita, Y. Kita, T. Kitamura, Y. Sato, and M. Mori Tetrahedron 62 2006 10518
40. D.A. Kummer, J.B. Brenneman, and S.F. Martin Tetrahedron 62 2006 11437
41. Y.D. Zhang, Y.F. Tang, T.P. Luo, J. Shen, J.H. Chen, and Z. Yang Org. Lett. 8 2006 107
42. L. Evanno, A. Deville, B. Bodo, and B. Nay Tetrahedron Lett. 48 2007 4331
43. F.D. Boyer, and I. Hanna Org. Lett. 9 2007 715
44. P.R. Krishna, and M. Narsingam Tetrahedron Lett. 48 2007 8721
45. M. Movassaghi, G. Piizzi, D.S. Siegel, and G. Piersanti Tetrahedron Lett. 50 2009 5489
46. D.S. Siegel, G. Piizzi, G. Piersanti, and M. Movassaghi J. Org. Chem. 74 2009 9292
47. S. Vuong, M.M. Rodriguez-Fernandez, B. Renoux, and C. Len Carbohydr. Res. 345 2010 324
48. E.M. Codesido, L. Castedo, and J.R. Granja Org. Lett. 3 2001 1483
49. F.-D. Boyer, I. Hanna, and L. Ricard Org. Lett. 3 2001 3095
50. M. Mori, T. Kitamura, N. Sakakibara, and Y. Sato Org. Lett. 2 2000 543
51. M. Mori, T. Kitamura, and Y. Sato Synthesis 2001 654
52. Y.-K. Yang, and J. Tae Synlett 2003 2017
53. J. Tae, and D.-W. Hahn Tetrahedron Lett. 45 2004 3757
54. B.P. Peppers, and S.T. Diver J. Am. Chem. Soc. 126 2004 9524
55. E. Groaz, D. Banti, and M. North Adv. Synth. Catal. 349 2007 142
56. F.-D. Boyer, and I. Hanna Eur. J. Org. Chem. 2008 4938
57. H. Wakamatsu, M. Sakagami, M. Hanata, M. Takeshita, and M. Mori Macromol. Symp. 293 2010 5
58. M. Turlington, Y. Du, S.G. Ostrum, V. Santosh, K. Wren, T. Lin, M. Sabat, and L. Pu J. Am. Chem. Soc. 133 2011 11780
59. For the synthesis of macrocyclic compounds via ring-closing enyne metathesis, see: Ref. 3b, 8c and E.C. Hansen, and D. Lee J. Am. Chem. Soc. 125 2003 9582
60. E.C. Hansen, and D. Lee J. Am. Chem. Soc. 126 2004 15074
61. M.E. Grimwood, and H.C. Hansen Tetrahedron 65 2009 8132
62. J.J. Lippstreu, and B.F. Straub J. Am. Chem. Soc. 127 2005 7444
63. J.F. Teichert, S. Zhang, A.W. van Zijl, J.W. Slaa, A.J. Minnaard, and B.L. Feringa Org. Lett. 12 2010 4658
64. K. Hammer, and K. Undheim Tetrahedron 53 1997 10603
65. Terminal alkynes were not suitable substrates also see: Ref. 6a, 13 and A.G.M. Barrett, S.P.D. Baugh, D.C. Braddock, K. Flack, V.C. Gibson, M.R. Giles, E.L. Marshall, P.A. Procopiou, A.J.P. White, and D.J. Williams J. Org. Chem. 63 1998 7893
66. V. Gracias, A.F. Gasiecki, and S.W. Djuric Tetrahedron Lett. 46 2005 9049
67. M. Mori, N. Sakakibara, and A. Kinoshita J. Org. Chem. 63 1998 6082
68. G.C. Lloyd-Jones, R.G. Margue, and J.G. de Vries Angew. Chem., Int. Ed. 44 2005 7442
69. A.G.D. Grotevendt, J.A.M. Lummiss, M.L. Mastronardi, and D.E. Fogg J. Am. Chem. Soc. 133 2011 15918