Base-assisted intramolecular 6-acetoxypyranone-acetylene [5+2] cycloaddition. Synthesis and reactivity of novel oxa-tricyclo[5.3.1.0 1,5]undecenones

Tetrahedron

Volumn 61, Issue 12, 2005, Pages 3025-3032

  Celanire, Sylvain ^a,b   Marlin, Frederic ^a   Baldwin, Jack E ^a   Adlington, Robert M ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UCB PHARMA   (Belgium)

Author keywords

3 Oxidopyrilium ylide; Acetylenic dipolarophiles; Intramolecular 5+2 cycloaddition; Tricyclo 5.3.1.0 undecane; Tropolone

Indexed keywords

3,11 DIOXATRICYCLO[5.3.1.0 1,5 ]UNDECA 5,9 DIEN 8 ONE DERIVATIVE; ACETYLENE DERIVATIVE; ACID; FURFURYL ALCOHOL; METHANOL DERIVATIVE; OXYGEN; PYRAN DERIVATIVE; TRICYCLIC AROMATIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 14744270943     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.113     Document Type: Article

References (63)

1. For excellent reviews, see: (a) Chiu, P.; Lautens, M. Using Ring-Opening Reactions of Oxabicyclic Compounds as a Strategy in Organic Synthesis. In Stereoselective Heterocyclic Synthesis II; Topics in Current Chemistry; Springer: Berlin, 1997; Vol. 190, pp 1-85. (b) Yet, L. Chem. Rev. 2000, 100, 2963.
2. For excellent reviews, see: (a) Chiu, P.; Lautens, M. Using Ring-Opening Reactions of Oxabicyclic Compounds as a Strategy in Organic Synthesis. In Stereoselective Heterocyclic Synthesis II; Topics in Current Chemistry; Springer: Berlin, 1997; Vol. 190, pp 1-85. (b) Yet, L. Chem. Rev. 2000, 100, 2963.
3. For excellent reviews, see: (a) Chiu, P.; Lautens, M. Using Ring-Opening Reactions of Oxabicyclic Compounds as a Strategy in Organic Synthesis. In Stereoselective Heterocyclic Synthesis II; Topics in Current Chemistry; Springer: Berlin, 1997; Vol. 190, pp 1-85. (b) Yet, L. Chem. Rev. 2000, 100, 2963.
4. G. Mehta, and J.D. Umarye Org. Lett. 4 2002 1063
5. P. Gerber, and P. Vogel Helv. Chim. Acta 84 2001 1363
6. A.M. Montaña, F. Garcia, and P.M. Gríma Tetrahedron 55 1999 5483
7. H.M.L. Davies, G. Ahmed, and M.R. Churchill J. Am. Chem. Soc. 118 1996 10774
8. D.R. Williams, J.W. Benbow, J.G. McNutt, and E.E. Allen J. Org. Chem. 60 1995 833
9. R. Huisgen A. Padwa 1,3-Dipolar Cycloaddition Chemistry 1984 Wiley-Interscience New York 1 176
10. S. Kobayashi K.A. Jørgensen Cycloaddition Reactions in Organic Synthesis 2002 Wiley-VCH Weiheim
11. A. Padwa W.H. Pearson Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products 2002 Wiley New York
12. P.A. Wender, K.D. Rice, and M.E. Schnute J. Am. Chem. Soc. 119 1997 7897
13. N. Ohmori J. Chem. Soc., Perkin Trans. 1 2002 755
14. W.E. Bauta, J. Booth, M.E. Bos, M. DeLuca, L. Diorazio, T.J. Donohoe, C. Frost, N. Magnus, P. Magnus, J. Mendoza, P. Pye, J.G. Tarrant, S. Thom, and F. Ujjainwalla Tetrahedron 52 1996 14081
15. J.C. Lee, and J.K. Cha J. Am. Chem. Soc. 123 2001 3243
16. J.E. Baldwin, A.V.W. Mayweg, G.J. Pritchard, and R.M. Adlington Tetrahedron Lett. 44 2003 4543
17. R.M. Adlington, J.E. Baldwin, A.V.W. Mayweg, and G.J. Pritchard Org. Lett. 4 2002 3009
18. J.E. Baldwin, A.V.W. Mayweg, K. Neumann, and G.J. Pritchard Org. Lett. 1 1999 1933
19. J.E. Baldwin, S.P. Romeril, V. Lee, and T.D.W. Claridge Org. Lett. 3 2001 1145
20. N.R. Irlapati, J.E. Baldwin, R.M. Adlington, G.J. Pritchard, and A. Cowley Org. Lett. 5 2003 2351
21. M. Holik, and I. Kurhr J. Chem. Soc., Chem. Commun. 1973 65
22. A.I. Scott, and E.L. Guilford J. Am. Chem. Soc. 93 1971 3534
23. P. Seephonkai, M. Isaka, P. Kittakoop, S. Trakulnaleamsai, R. Rattanajak, M. Tanticharoen, and Y. Thebtaranonth J. Antibiotics 54 2001 751 752
24. For reviews and applications on [4+3] cycloadditions, see: (a) R. Noyori, and Y. Hayakawa Org. React. 29 1983 163
25. H.M.R. Hoffmann Angew. Chem., Int. Ed. Engl. 23 1984 1
26. J.H. Rigby, and F.C. Pigge Org. React. 51 1997 351
27. K. Lee, and J.K. Cha Org. Lett. 1 1999 523
28. [4+2]-cycloadditions: (e) R.S. Orugunty, D.L. Wright, M.A. Battiste, and K.A. Abboud Org. Lett. 4 2002 1997
29. B. Wockenfub, C. Wolff, and W. Tochtermann Tetrahedron 53 1997 13703
30. For original works, see: (a) J.B. Hendrickson, and J.S. Farina J. Org. Chem. 45 1980 3359
31. P.G. Sammes, and L. Street J. Chem. Soc., Perkin Trans. 1 1986 281
32. A.R. Katritzky, and N. Dennis Chem. Rev. 89 1989 827
33. J.L. Mascareñas M. Harmata Advances in Cycloaddition Vol. 6 1999 JAI Stanford, CT 1 54
34. J.L. Mascareñas, A. Rumbo, and L. Castedo J. Org. Chem. 62 1997 8620
35. J.L. Mascareñas, I. Perez, A. Rumbo, and L. Castedo Synlett 1997 81
36. N. Ohmori, M. Yoshimura, and K. Ohkata Heterocycles 45 1997 2097
37. A. Padwa, and M.D. Weingarten Chem. Rev. 96 1996 223
38. M.P. Doyle, M.A. McKervey, and T. Ye Modern Catalytic Methods for Organic Synthesis with Diazo Compounds. From Cyclopropanes to Ylides 1998 Wiley-Interscience New York pp 355-432
39. F. Lopez, L. Castedo, and J.L. Mascareñas Chem. Eur. Joc. 8 2002 884
40. A. Delgado, L. Castedo, and J.L. Mascareñas Org. Lett. 4 2002 3987
41. N. Ohmori, T. Miazaki, S. Kojima, and K. Ohkata Chem. Lett. 2001 906
42. P. Magnus, and L. Shen Tetrahedron 55 1999 3553
43. K.A. Marshall, A.K. Mapp, and C.H. Heathcock J. Org. Chem. 61 1996 9135
44. H.-Y. Lee, J.-H. Sohn, and H.Y. Kim Tetrahedron Lett. 42 2001 1695
45. F. Richter, C. Maichle-Mossner, and M.E. Maier Synlett 7 2002 1097
46. J.R. Rodriguez, L. Castedo, and J.L. Mascareñas J. Org. Chem. 65 2000 2528
47. D.M. Hodgson, R. Glen, G.H. Grant, and A.J. Redgrave J. Org. Chem. 68 2003 581
48. D.M. Hodgson, A.H. Labande, and F.Y.T.M. Pierard Synlett 1 2003 59
49. T. Graening, W. Friedrichsen, J. Lex, and H.-G. Schmalz Angew. Chem., Int. Ed. 41 2002 1524
50. A. Padwa J. Organomet. Chem. 610 2000 88
51. S. Muthusamy, S.A. Babu, C. Gunanathan, E. Suresh, P. Dastidar, and R.V. Jasra Tetrahedron 56 2000 6307
52. S. Kitagaki, M. Anada, O. Kataoka, K. Matsumo, C. Umeda, N. Watanabe, and S.-i. Hashimoto J. Am. Chem. Soc. 121 1999 1417
53. B.J. McBride, and M.E. Garst Tetrahedron 49 1993 2839
54. T.-L. Ho, and S.G. Sapp Synth. Commun. 13 1983 207
55. E.A. Couladouros, and M.P. Georgiadis J. Org. Chem. 51 1986 2725
56. T. Taniguchi, H. Ohnishi, and K. Ogasawara Chem. Commun. 1996 1477
57. J.E. Baldwin, P.G. Bulger, and R. Marquez Tetrahedron 58 2002 5441
58. M.H. Haukaas, and G.A. O'Doherty Org. Lett. 3 2001 3899
59. D.R. Williams, J.W. Benbow, and E.E. Allen Tetrahedron Lett. 31 1990 6769
60. J. Fayos, J. Clardy, L.J. Dolby, and T. Farnham J. Org. Chem. 42 1977 1349
61. C. Lauret Tetrahedron: Asymmetry 12 2001 2359
62. M.-H. Filippini, R. Faure, and J. Rodriguez J. Org. Chem. 60 1995 6872
63. E.J. Corey, and M.C. Noe J. Am. Chem. Soc. 118 1996 319