O→C rearrangements: a powerful strategy for the synthesis of functionalised carbocycles

Tetrahedron

Volumn 63, Issue 15, 2007, Pages 3081-3092

  Meek, Simon J ^a   Harrity, Joseph P A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

Carbocycles; Oxocarbenium ions; Rearrangements; Stereoselective

Indexed keywords

CARBON; DIOXANE; OXYGEN;

CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW; SYNTHESIS;

EID: 33947181542     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.01.004     Document Type: Review

References (67)

1. Concerted processes such as the Claisen rearrangement will not form part of this review, for a recent discussion of this area see:. Martin Castro A.M. Chem. Rev. 104 (2004) 2939
2. Ferrier R.J. J. Chem. Soc., Perkin Trans. 1 (1979) 1455
3. Ferrier R.J., and Middleton S. Chem. Rev. 93 (1993) 2779
4. Machado A.S., Olesker A., and Lukacs G. Carbohydr. Res. 135 (1985) 231
5. Chida N., Ohtsuka M., Ogura K., and Ogawa S. Bull. Chem. Soc. Jpn. 64 (1991) 2118
6. Adam S. Tetrahedron Lett. 29 (1988) 6589
7. László P., and Dudon A. J. Carbohydr. Chem. 11 (1992) 587
8. Chida N., Ohtsuka M., and Ogawa S. J. Org. Chem. 58 (1993) 444
9. Das S.K., Mallet J.-M., and Sinaÿ P. Angew. Chem., Int. Ed. 36 (1997) 493
10. Baldwin J.E., and Lush M.J. Tetrahedron 38 (1982) 2939
11. Sollogoub M., Mallet J.-M., and Sinaÿ P. Tetrahedron Lett. 39 (1998) 3471
12. Dixon D.J., Ley S.V., and Tate E.W. J. Chem. Soc., Perkin Trans. 1 (2000) 1829
13. Buffet M.F., Dixon D.J., Edwards G.L., Ley S.V., and Tate E.W. Synlett (1997) 1055
14. Buffet M.F., Dixon D.J., Ley S.V., and Tate E.W. Synlett (1998) 1091
15. Buffet M.F., Dixon D.J., Edwards G.L., Ley S.V., and Tate E.W. J. Chem. Soc., Perkin Trans. 1 (2000) 1815
16. Buffet M.F., Dixon D.J., Ley S.V., Reynolds D.J., and Storer R.I. Org. Biomol. Chem. 2 (2004) 1145
17. Dixon D.J., Ley S.V., and Reynolds D.J. Angew. Chem., Int. Ed. 39 (2000) 3622
18. Dixon D.J., Ley S.V., and Reynolds D.J. Chem.-Eur. J. 8 (2002) 1621
19. Dixon D.J., Ley S.V., and Tate E.W. J. Chem. Soc., Perkin Trans. 1 (1999) 2665
20. Dixon D.J., Ley S.V., and Tate E.W. J. Chem. Soc., Perkin Trans. 1 (2000) 2385
21. Dixon D.J., Ley S.V., and Tate E.W. Synlett (1998) 1093
22. Dixon D.J., Ley S.V., and Tate E.W. J. Chem. Soc., Perkin Trans. 1 (1998) 3125
23. Tate E.W., Dixon D.J., and Ley S.V. Org. Biomol. Chem. 4 (2006) 1698
24. Zhang Y., Reynolds N.T., Manju K., and Rovis T. J. Am. Chem. Soc. 124 (2002) 9720
25. Zhang Y., and Rovis T. Tetrahedron 59 (2003) 8979
26. Frein J.D., and Rovis T. Tetrahedron 62 (2006) 4573
27. Shenoy S.R., and Woerpel K.A. Org. Lett. 7 (2005) 1157
28. Petasis N.A., and Lu S.-P. J. Am. Chem. Soc. 177 (1995) 6394
29. Baldwin J.E. J. Chem. Soc., Chem. Commun. (1976) 734
30. Baldwin J.E., Cutting J., Dupont W., Kruse L., Silberman L., and Thomas R.C. J. Chem. Soc., Chem. Commun. (1976) 736
31. Baldwin J.E., and Kruse L. J. Chem. Soc., Chem. Commun. (1977) 233
32. Baldwin J.E., Thomas R.C., Kruse L., and Silberman L. J. Org. Chem. 42 (1977) 3846
33. Petasis N.A., and Lu S.-P. Tetrahedron Lett. 37 (1996) 141
34. (+)-Phorboxazole A:. Smith III A.B., Minbiole K.P., Verhoest P.R., and Schelhaas M. J. Am. Chem. Soc. 123 (2001) 10942
35. Smith III A.B., Razler M.T., Ciavarri P.J., Hirose T., and Ishikawa T. Org. Lett. 20 (2005) 4399
36. (+)-Spongistatin 1:. Smith III A.B., Sfouggatakis C., Gotchev B.D., Shirakami S., Bauer D., Zhu W., and Doughty V.A. Org. Lett. 20 (2004) 3637
37. (+)-Zampanolide and (+)-dactylolide:. Smith III A.B., Safonov I.G., and Corbett M.R. J. Am. Chem. Soc. 124 (2002) 11102
38. (-)-Kendomycin:. Smith III A.B., Mesaros E.F., and Meyer E.A. J. Am. Chem. Soc. 127 (2005) 6948
39. Smith III A.B., Mesaros E.F., and Meyer E.M. J. Am. Chem. Soc. 128 (2006) 5292
40. (+)-Sorangicin A:. Smith III A.B., Fox R.J., and Vanecko J.A. Org. Lett. 14 (2005) 3099
41. (-)-Clavosolide A:. Smith III A.B., and Simov V. Org. Lett. 8 (2006) 3315
42. Evans D.A., Bartroli J., and Shih T.L. J. Am. Chem. Soc. 103 (1981) 2127
43. O'Neil K.E., Kingree S.V., and Minbiole P.C. Org. Lett. 7 (2005) 515
44. Coleman R.S., Guernon J.M., and Roland J.T. Org. Lett. 2 (2000) 277
45. Suzuki T., Inui M., Hosokawa S., and Kobayashi S. Tetrahedron Lett. 44 (2003) 3713
46. Suzuki T., Inui M., Hosokawa S., Nakazaki A., and Kobayashi S. Tetrahedron Lett. 46 (2005) 3245
47. Zwahlen K.D., Horton W.J., and Fujimoto G.I. J. Am. Chem. Soc. 79 (1957) 3131
48. Weill-Raynal J. Synthesis (1969) 49
49. Colvin E.W., Raphael R.A., and Roberts J.S. J. Chem. Soc., Chem. Commun. (1971) 858
50. Colvin E.W., Malchenko S., Raphael R.A., and Roberts J.S. J. Chem. Soc., Perkin Trans. 1 (1973) 1989
51. Holland H.L., MacLean D.B., Rodrigo R.G.A., and Manske R.F.H. Tetrahedron Lett. (1975) 4323
52. Kelly T.R., Ohashi N., Armstrong-Chong R.J., and Bell S.H. J. Am. Chem. Soc. 108 (1986) 7100
53. Kelly T.R., Bell S.H., Ohashi N., and Armstrong-Chong R.J. J. Am. Chem. Soc. 110 (1988) 6471
54. Mehta G., and Bera M.K. Tetrahedron Lett. 47 (2006) 689
55. Sollogoub M., Mallet J.-M., and Sinaÿ P. Angew. Chem., Int. Ed. 39 (2000) 362
56. Sollogoub M., Pearce A.J., Hérault A., and Sinaÿ P. Tetrahedron: Asymmetry 11 (2000) 283
57. Trost B.M., Runge T.R., and Jungheim L.N. J. Am. Chem. Soc. 102 (1980) 2840
58. Trost B.M., and Runge T.R. J. Am. Chem. Soc. 103 (1981) 2485
59. Trost B.M., and Runge T.R. J. Am. Chem. Soc. 103 (1981) 7550
60. Trost B.M., and Runge T.R. J. Am. Chem. Soc. 103 (1981) 7559
61. Carbery D.R., Reignier S., Myatt J.W., Miller N.D., and Harrity J.P.A. Angew. Chem., Int. Ed. 41 (2002) 2584
62. Carbery D.R., Miller N.D., and Harrity J.P.A. Chem. Commun. (2002) 1546
63. Carbery D.R., Reignier S., Miller N.D., Adams H., and Harrity J.P.A. J. Org. Chem. 68 (2003) 4392
64. Meek S.J., Pradaux F., Carbery D.R., Demont E.H., and Harrity J.P.A. J. Org. Chem. 70 (2005) 10046
65. Deleuze A., Menozzi C., Sollogoub M., and Sinaÿ P. Angew. Chem., Int. Ed. 43 (2004) 6680
66. Meek S.J., Pradaux F., Demont E.H., and Harrity J.P.A. Org. Lett. 8 (2006) 5597
67. Du Roizel B., Sollogoub M., Pearce A.J., and Sinaÿ P. Chem. Commun. (2000) 1507