Synthesis of 2(3H)-furanones via electrophilic cyclization

Journal of Organic Chemistry

Volumn 73, Issue 7, 2008, Pages 2662-2667

  Just, Ziwei W ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUPS; ORGANIC ACIDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ELECTROPHILIC CYCLIZATION; FURANONES;

ESTERS;

ALKYNE; FURANONE DERIVATIVE; IODINE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; SUBSTITUTION REACTION; SYNTHESIS;

ALKYNES; CYCLIZATION; ESTERS; FURANS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 41649093170     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702666j     Document Type: Article

References (69)

1. (a) Yao, Y. S. Chem. Rev. 1964, 64, 353.
2. (b) Yao, Y. S. Chem. Rev. 1976, 76, 625.
3. (a) Higuchi, Y.; Shimoma, F.; Ando, M. J. Nat. Prod. 2003, 66, 810.
4. (b) Hislop, J.-A.; Hunt, M. B.; Fielder, S.; Rowan, D. D. J. Agric. Food Chem. 2004, 52, 7075.
5. (c) Frediani, P.; Rosi, L.; Frediani, M.; Bartolucci, C.; Bambagiotti-Alberti, M. J. Agric. Food Chem. 2007, 55, 3877.
6. Kubo, M.; Fujii, T.; Hioki, H.; Tanaka, M.; Kawazub, K.; Fukuyama, Y. Tetrahedron Lett. 2001, 42, 1081.
7. Amal Raj, A.; Raghunathan, R.; SrideviKumari, M. R.; Raman, N. Bioorg. Med. Chem. 2003, 11, 407.
8. For a review, see: Larock, R. C. In Acetylene Chemistry, Chemistry, Biology, and Material Science; Diederich, F., Stang, P. J., Tykwinski, R. R., Eds.; Wiley-VCH: New York, 2005; Chapter 2, pp 51-99.
9. Zhang, X.; Campo, M. A.; Yao, T.; Larock, R. C. Org. Lett. 2005, 7, 763.
10. (a) Waldo, J. P.; Larock, R. C. Org. Lett. 2005, 7, 5203.
11. (b) Waldo, J. P.; Larock, R. C. J. Org. Chem. 2007, 72, 9643.
12. Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 1432.
13. (a) Larock, R. C.; Yue, D. Tetrahedron Lett. 2001, 42, 6011.
14. (b) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905.
15. (c) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 651.
16. Ren, X.-F.; Konaklieva, M. I.; Shi, H.; Dickey, S.; Lim, D. V.; González, J.; Turos, E. J. Org. Chem. 1998, 63, 8898.
17. (a) Barluenga, J.; Trincado, M.; Rublio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
18. (b) Muhammad, A.; Knight, D. W. Tetrahedron Lett. 2004, 45, 539.
19. (c) Yue, D.; Larock, R. C. Org. Lett. 2004, 6, 1037.
20. (d) Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2006, 71, 62.
21. (e) Yue, D.; Yao, T.; Larock, R. C. J. Comb. Chem. 2005, 7, 809.
22. Zhou, C.; Dubrovsky, A. V.; Larock, R. C. J. Org. Chem. 2006, 71, 1626.
23. (a) Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; González, J. M. J. Am. Chem. Soc. 2003, 125, 9028.
24. (b) Yue, D.; Della Cá, N.; Larock, R. C. Org. Lett. 2004, 6, 1581.
25. (c) Yue, D.; Della Cá, N.; Larock, R. C. J. Org. Chem. 2006, 71, 3381.
26. Zhang, X.; Sarkar, S.; Larock, R. C. J. Org. Chem. 2006, 71, 236.
27. (a) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432.
28. (b) Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 10292.
29. Marshall, J. A.; Yanik, M. M. J. Org. Chem. 1999, 64, 3798.
30. Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc., Chem. Commun. 1998, 2207.
31. (a) Bew, S. P.; Knight, D. W. J. Chem. Soc., Chem. Commun. 1996, 1007.
32. (b) Djuardi, E.; McNelis, E. Tetrahedron Lett. 1999, 40, 7193.
33. (c) Sniady, A.; Wheeler, K. A.; Dembinski, R. Org. Lett. 2005, 7, 1769.
34. (d) Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164.
35. (e) Yao, T.; Zhang, X.; Larock, R. C. J. Org. Chem. 2005, 70, 7679.
36. (f) Liu, Y.; Zhou, S. Org. Lett. 2005, 7, 4609.
37. (a) Yao, T.; Larock, R. C. Tetrahedron Lett. 2002, 43, 7401.
38. (b) Yao, T.; Larock, R. C. J. Org. Chem. 2003, 68, 5936.
39. (c) Oliver, M. A.; Gandour, R. D. J. Org. Chem. 1984, 49, 558.
40. (d) Biagetti, M.; Bellina, F.; Carpita, A.; Stabile, P.; Rossi, R. Tetrahedron 2002, 58, 5023.
41. (e) Rossi, R.; Carpita, A.; Bellina, F.; Stabile, P.; Mannina, L. Tetrahedron 2003, 59, 2067.
42. (a) Huang, Q.; Hunter, J. A.; Larock, R. C. Org. Lett. 2001, 3, 2973.
43. (b) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437.
44. (a) Yao, T.; Campo, M. A.; Larock, R. C. Org. Lett. 2004, 6, 2677.
45. (b) Yao, T.; Campo, M. A.; Larock, R. C. J. Org. Chem. 2005, 70, 3511.
46. Kesharwani, T.; Worlikar, S. A.; Larock, R. C. J. Org. Chem. 2006, 71, 2307.
47. Arcadi, A.; Cacchi, S.; Di, Giuseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409.
48. Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551.
49. Lepore, S. D.; He, Y. J. Org. Chem. 2005, 70, 4546.
50. (a) White, W. L.; Ricciardelli, K. L.; Chaguturu, M. K. U.S. patent 4704161 A, 1986.
51. (b) Meyer, A.; Flammang, M.; Wermuth, C. G. Synthesis 1976, 832.
52. (a) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135.
53. (b) Chui, C. C.; Jordan, F. J. J. Org. Chem. 1994, 59, 5763.
54. Sleeman, M. J.; Meehan, G. V. Tetrahedron 1989, 30, 3345.
55. (a) Fu, C.; Ma, S. Eur. J. Org. Chem. 2005, 3942.
56. (b) Ma, S.; Wu, S. Tetrahedron Lett. 2001, 42, 4075.
57. (c) Ma, S.; Pan, F.; Hao, X.; Huang, X. Synlett 2004, 85.
58. Jung, M. E.; Piizzi, G. Chem. Rev. 2005, 105, 1735.
59. For leading reviews of the Heck reaction, see: (a) De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
60. (b) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371.
61. (c) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
62. (d) Overman, L. E. Pure Appl. Chem. 1994, 66, 1423.
63. For reviews, see: (a) Campbell, I. B. The Sonogashira Cu-Pd-Catalyzed Alkyne Coupling Reaction. Organocopper Reagents; Taylor, R. T. K., Ed.; IRL Press: Oxford, UK, 1994; pp 217-235.
64. (b) Sonogashira, K.; Takahashi, S. Yuki Gosei Kagaku Kyokaishi 1993, 51, 1053.
65. (c) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 521-549.
66. For reviews, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
67. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
68. (c) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 2.
69. Friesen, R. W.; Ducharme, Y.; Ball, R. G.; Blouin, M.; Boulet, L.; Cote, B.; Frenette, R.; Girard, M.; Guay, D.; Huang, Z.; Jones, T. R.; Laliberte, F.; Lynch, J. J.; Mancini, J.; Martins, E.; Masson, P.; Muise, E.; Pon, D. J.; Siegl, P. K. S.; Styhler, A.; Tsou, N. N.; Turner, M. J.; Young, R. N.; Girard, Y. J. Med. Chem. 2003, 46, 2413.