One-pot transformation of simple furans into 4-Hydroxy-2-cyclopentenones in water

Angewandte Chemie - International Edition

Volumn 53, Issue 48, 2014, Pages 13201-13205

  Kalaitzakis, Dimitris ^a   Triantafyllakis, Myron ^a   Alexopoulou, Ioanna ^a   Sofiadis, Manolis ^a   Vassilikogiannakis, Georgios ^a  

^a UNIVERSITY OF CRETE   (Greece)

Author keywords

Cyclopentenones; Furan oxidation; Intramolecular aldol; Singlet oxygen; Sustainable chemistry

Indexed keywords

AROMATIC COMPOUNDS; KETONES; OXYGEN;

CYCLOPENTENONES; FURAN OXIDATION; INTRAMOLECULAR ALDOL; SINGLET OXYGEN; SUSTAINABLE CHEMISTRY;

ORGANIC POLLUTANTS;

4-HYDROXY-2-CYCLOPENTENONE; CYCLOPENTANE DERIVATIVE; FURAN DERIVATIVE; WATER;

CHEMICAL STRUCTURE; CHEMISTRY;

CYCLOPENTANES; FURANS; MOLECULAR STRUCTURE; WATER;

EID: 84915751226     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201407477     Document Type: Article

References (68)

1. For selected recent examples of natural products containing the scaffold, see: a) S. Greff, M. Zubia, G. Genta-Jouve, L. Massi, T. Perez, O. P. Thomas, J. Nat. Prod. 2014, 77, 1150-1155;
2. b) J. Urban, C. J. Dahlberg, B. J. Carroll,W. Kaminsky, Angew. Chem. Int. Ed. 2013, 52, 1553-1555;
3. Angew. Chem. 2013, 125, 1593-1595;
4. c) V. Schmidts, M. Fredersdorf, T. Loabken, A. Porzel, N. Arnold, L.Wessjohann, C. M. Thiele, J. Nat. Prod. 2013, 76, 839-844;
5. d) S. Wang, S.-S. Liu, Z.-M. Lin, R.-J. Li, X.-N. Wang, J.-C. Zhou, H.-X. Lou, J. Asian Nat. Prod. Res. 2013, 15, 473-481;
6. e) H. Shi, S. Yu,D. Liu, L. van Ofwegen, P. Proksch,W. Lin, Mar. Drugs 2012, 10, 1331-1344.
7. For a review, see: a) S. P. Roche, D. J. Aitken, Eur. J. Org. Chem. 2010, 5339-5358;
8. For selected examples after 2010, see: b) G. Singh, A. Meyer, J. Aub, J. Org. Chem. 2014, 79, 452-458;
9. c) A. Jose, K. C. S. Lakshmi, E. Suresh, V. Nair, Org. Lett. 2013, 15, 1858-1861;
10. d) M. Ahmar, S. Thom, B. Cazes, Eur. J. Org. Chem. 2012, 7093-7105;
11. e) B. Darses, I. N. Michaelides, F. Sladojevich, J.W. Ward, P. R. Rzepa, D. J. Dixon, Org. Lett. 2012, 14, 1684-1687;
12. f) M. Brasholz, B. Dugovič, H.-U. Reissig, Synthesis 2010, 3855-3864.
13. a) D. Fisher, L. I. Palmer, J. E. Cook, J. E. Davis, J. Read deAlaniz, Tetrahedron 2014, 70, 4105-4110;
14. b) C. Piutti, F. Quartieri, Molecules 2013, 18, 12290-12312;
15. c) J. P. Henschke, Y. Liu, X. Huang, Y. Chen, D. Meng, L. Xia, X. Wei, A. Xie, D. Li, Q. Huang, T. Sun, J. Wang, X. Gu, X. Huang, L. Wang, J. Xiao, S. Qiu, Org. Process Res. Dev. 2012, 16, 1905-1916;
16. d) K. Ulbrich, P. Kreitmeier, O. Reiser, Synlett 2010, 2037-2040;
17. e) O. Nieto Faza, C. S. López, R. Olvarez,. R. de Lera, Chem. Eur. J. 2004, 10, 4324-4333;
18. f) G. Piancatelli, Heterocycles 1982, 19, 1735-1744;
19. g) G. Piancatelli, A. Scettri, S. Barbadoro, Tetrahedron Lett. 1976, 17, 3555-3558.
20. a) J. Mulzer, G. Giester, M. Gilbert, Helv. Chim. Acta 2005, 88, 1560-1579;
21. b) E. Pinot, A. Guy, A.-L. Guyon, J.-C. Rossi, T. Durand, Tetrahedron: Asymmetry 2005, 16, 1893-1895;
22. c) S. Caddick, S. Khan, L. M. Frost, N. J. Smith, S. Cheung, G. Pairaudeau, Tetrahedron 2000, 56, 8953-8958;
23. d) G. Adembri, G. Giorgi, R. L. Lampariello, M. L. Paoli, A. Sega, J. Chem. Soc. Perkin Trans. 1 2000, 2649-2656;
24. e) S. Al-Busafi,M. G. B. Drew, T. Sanders, R. C. Whitehead, Tetrahedron Lett. 1998, 39, 1647-1650;
25. f) G. Piancatelli, M. D'Auria, F. D'Onofrio, Synthesis 1994, 867-889;
26. g) T. Shono, Y. Matsumura, H. Hamaguchi, K. Nakamura, Chem. Lett. 1976, 1249-1252.
27. For furan photooxidations see: a) C. S. Foote, M. T. Wuesthoff, S. Wexler, I. G. Burstain, R. Denny, G. O. Schenck, K. H. Schulte-Elte, Tetrahedron 1967, 23, 2583-2599;
28. b) K. Gollnick, A. Griesbeck, Angew. Chem. Int. Ed. Engl. 1983, 22, 726-727;
29. Angew. Chem. 1983, 95, 751;
30. c) K. Gollnick, A. Griesbeck, Tetrahedron 1985, 41, 2057-2068;
31. d) B. L. Feringa, Recl. Trav. Chim. Pays-Bas 1987, 106, 469-488.
32. a) E. J. Corey, M. M. Mehrotra, J. Am. Chem. Soc. 1984, 106, 3384;
33. b) B. B. Snider, Z. Shi, J. Am. Chem. Soc. 1992, 114, 1790-1800;
34. c) B. B. Snider, Z. Shi, S. V. O'Neil, K. D. Kreutter, T. L. Arakaki, J. Org. Chem. 1994, 59, 1726-1729;
35. d) T.-C. Kao, G. J. Chuang, C.-C. Liao, Angew. Chem. Int. Ed. 2008, 47, 7325-7327;
36. Angew. Chem. 2008, 120, 7435-7437.
37. G. Vassilikogiannakis, M. Stratakis, Angew. Chem. Int. Ed. 2003, 42, 5465-5468;
38. Angew. Chem. 2003, 115, 5623-5626.
39. a) T. Montagnon, D. Noutsias, I. Alexopoulou, M. Tofi, G. Vassilikogiannakis, Org. Biomol. Chem. 2011, 9, 2031-2039;
40. b) T. Montagnon, M. Tofi, G. Vassilikogiannakis, Acc. Chem. Res. 2008, 41, 1001-1011;
41. c) D. Noutsias, I. Alexopoulou, T. Montagnon, G. Vassilikogiannakis, Green Chem. 2012, 14, 601-604.
42. For rearrangement of 2→3, see: a) A. Scettri, G. Piancatelli, M. D'Auria, G. David, Tetrahedron 1979, 35, 135-138;
43. b) M. D'Auria, Heterocycles 2000, 52, 185-194, and references therein;
44. c) G. Stork, C. Kowalski, G. Garcia, J. Am. Chem. Soc. 1975, 97, 3258-3260.
45. a) S. Das, S. Chandrasekhar, J. S. Yadav, R. Grée, Chem. Rev. 2007, 107, 3286-3337;
46. b) P.W. Collins, S.W. Djuric, Chem. Rev. 1993, 93, 1533-1564;
47. c) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, Wiley-VCH, Weinheim, 1996.
48. L. Novak, C. Szantay, T. Meisel, J. Aszodi, E. Szabo, J. Fekete, Tetrahedron 1985, 41, 435-450.
49. For recent selected examples, see: a) J.-Q. Liu, Y.-F. Yang, X.-Y. Li, E.-Q. Liu, Z.-R. Li, L. Zhou, Y. Li, M.-H. Qiu, Phytochemistry 2013, 96, 265-272;
50. b) R. Tohme, L. Al Aaraj, T. Ghaddar, H. Gali-Muhtasib, N. A. Saliba,N. Darwiche, Molecules 2013, 18, 8275-8288;
51. c) Y. Li, M.-C. Zhu, M.-L. Zhang, Y.-F. Wang, M. Dong, Q.-W. Shi, C.-H. Huo, F. Sauriol, H. Kiyota, Y.-C. Gu, B. Cong, Tetrahedron Lett. 2012, 53, 2601-2603;
52. d) Y. Deng, Y.-W. Chin, H.-B. Chai, E. C. de Blanco, L. B. S. Kardono, S. Riswan, D. D. Soejarto, N. R. Farnsworth, A. D. Kinghorn, Phytochem. Lett. 2011, 4, 213-217.
53. For the isolation of Untenone A, see: a) M. Ishibashi, S. Takeuchi, J. Kobayashi, Tetrahedron Lett. 1993, 34, 3749-3750;
54. For a synthesis of UntenoneA starting from furans, see: b) S. Al-Busafi, R. C.Whitehead, Tetrahedron Lett. 2000, 41, 3467-3470.
55. a) M. S. Schechter, N. Green, F. B. Laforge, J. Am. Chem. Soc. 1949, 71, 3165-3173;
56. b) L. Crombie, M. Elliott, Fortschr. Chem. Org. Naturst. 1961, 19, 120-164;
57. c) G. Piancatelli, M. D'Auria, A. Scettri, U.S Pat. 4413145, 1981
58. [Chem. Abstr. 1982, 96, 217332b].
59. a) A. Kobayashi, K. Yamashita, K. Ohshima, I. Yamamoto, Agric. Biol. Chem. 1971, 35, 1961-1965;
60. b) P. R. Chadwich, Mosquito News 1970, 30, 162-170;
61. c) M. Matsui, H. Meguro, Agric. Biol. Chem. 1964, 28, 27-31.
62. For selected examples, see: a) R. J. Capon, S. Singh, S. Ali, S. Sotheeswaran, Aust. J. Chem. 2005, 58, 18-20;
63. b) R. S. Compagnone, I. C. Piña, H. R. Rangel, F. Dagger, A. I. Suárez, M. V. R. Reddy, D. J. Faulkner, Tetrahedron 1998, 54, 3057-3068.
64. a) S. Tsukamoto, S. Takeuchi, M. Ishibashi, J. Kobayashi, J. Org. Chem. 1992, 57, 5255-5260;
65. b) J. Kobayashi, S. Tsukamoto, S. Takeuchi, M. Ishibashi, Tetrahedron 1993, 49, 5955-5960.
66. S. Al-Busafi, J. R. Doncaster, M. G. B. Drew, A. C. Regan, R. C. Whitehead, J. Chem. Soc. Perkin Trans. 1 2002, 476-484.
67. a) T. Newhouse, P. S. Baran, R.W. Hoffmann, Chem. Soc. Rev. 2009, 38, 3010-3021;
68. b) T. Gaich, P. S. Baran, J. Org. Chem. 2010, 75, 4657-4673.