Cationic gold(I)-catalyzed intramolecular cyclization of γ-hydroxyalkynones into 3(2H)-furanones

Journal of Organic Chemistry

Volumn 75, Issue 6, 2010, Pages 2123-2126

  Egi, Masahiro ^a   Azechi, Kenji ^a   Saneto, Moriaki ^a   Shimizu, Kaori ^a   Akai, Shuji ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATIONIC GOLD; CHEMICAL EQUATIONS; FURANONES; INTRAMOLECULAR CYCLIZATIONS;

GOLD COMPOUNDS;

CYCLIZATION;

2,3 DIHYDRO 4H PYRAN 4 ONE DERIVATIVE; 3 (2H) FURANONE DERIVATIVE; ALKYNE DERIVATIVE; FURANONE DERIVATIVE; GAMMA HYDROXYALKYNONE DERIVATIVE; GOLD; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

4-BUTYROLACTONE; ALKANES; CATALYSIS; CATIONS; CYCLIZATION; GOLD; HYDROXYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 77949789040     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100048j     Document Type: Article

References (54)

1. Geiparvarin: (a) Valenti, P. Fitoterapia. 1997, 68, 115, 115-126. Eremantho-lide: for recent total syntheses, see:
2. (b) Li, Y.; Hale, K. J. Org. Lett. 2007, 9, 1267-1270.
3. (c) Sass, D. C.; Heleno, V. C. G.; Lopes, J. L. C.; Constantino, M. G. Tetrahedron Lett. 2008, 49, 3877-3880. Jatrophone:
4. (d) Gonçalves de Moraes, V. L.; Rumjanek, V. M.; Calixto, J. B. Eur. J. Pharmacol. 1996, 312, 333-339.
5. (e) Han, Q.; Wiemer, D. F. J. Am. Chem. Soc. 1992, 114, 7692-7697. Pseurotin:
6. (f) Ishikawa, M.; Ninomiya, T.; Akabane, H.; Kushida, N.; Tsujiuchi, G.; Ohyama, M.; Gomi, S.; Shito, K.; Murata, T. Bioorg. Med. Chem. Lett. 2009, 19, 1457-1460.
7. (a) Woollard, J. McK. R.; Perry, N. B.; Weavers, R. T.; van Klink, J. W. Phytochemistry 2008, 69, 1313-1318.
8. (b) Asami, Y.; Kakeya, H.; Onose, R.; Yoshida, A.; Matsuzaki, H.; Osada, H. Org. Lett. 2002, 4, 2845-2848.
9. (c) Ando, O.; Satake, H.; Nakajima, M.; Sato, A.; Nakamura, T.; Kinoshita, T.; Furuya, K.; Haneishi, T. J. Antibiot. 1991, 44, 382-389.
10. (d) Kírmíztgül, S.; Gören, N.; Yang, S.-W.; Cordell, G. A.; Bozok-Johansson, C. J. Nat. Prod. 1997, 60, 378-381.
11. (e) Shiozawa, H.; Takahashi, M.; Takatsu, T.; Kinoshita, T.; Tanzawa, K.; Hosoya, T.; Furuya, K.; Takahashi, S.; Furihata, K.; Seto, H. J. J. Antibiot. 1995, 48, 357-362.
12. (f) Paul, M. C.; Zubia, E.; Ortega, M. J.; Salvá, J. Tetrahedron 1997, 53, 2303-2308.
13. (g) Edwards, R. L.; Maitland, D. J.; Oliver, C. L.; Pacey, M. S.; Shields, L.; Whalley, A. J. S. J. Chem. Soc. Perkin Trans. 1 1999, 715-719.
14. (h) Koga, T.; Moro, K.; Matsudo. T. J. Agric. Food Chem. 1998, 46, 946-951.
15. (i) Oh, H.; Lee, S.; Lee, H.-S.; Lee, D.-H.; Lee, S. Y.; Chung, H.-T.; Kim, T. S.; Kwon, T.-O. Phytochemistry 2002, 61, 175-179.
16. Jerris, P. J.; Smith, A. B., IlI J. Org. Chem. 1981, 46, 577-585.
17. Chimichi, S.; Boccalini, M.; Cosimelli, B.; Dall'Acqua, F.; Viola, G. Tetrahedron 2003, 59, 5215-5223.
18. Felman, S. W.; Jirkovsky, I.; Memoli, K. A.; Borella, L.; Wells, C.; Russell, J.; Ward, J. J. Med. Chem. 1992, 35, 1183-1190.
19. Mack, R. A.; Zazulak, W. I.; Radov, L. A.; Baer, J. E.; Stewart, J. D.; Elzer, P. H.; Kinsolving, C. R.; Georgiev, V. S. J. Med. Chem. 1988, 31 1910-1918.
20. Shin, S. S.; Byun, Y.; Lim, K. M.; Choi, J. K.; Lee, K.-W.; Moh, J. H.; Kim, J. K.; Jeong, Y. S.; Kim, J. Y.; Choi, Y. H.; Koh, H.-J.; Park, Y.-H.; Oh, Y. I.; Noh, M.-S.; Chung, S. J. Med. Chem. 2004, 47, 792-804.
21. Carotti, A.; Carrieri, A.; Chimichi, S.; Boccalini, M.; Cosimelli, B.; Gnerre, C.; Carotti, A.; Carrupt, P.-A.; Testa, B. Bioorg. Med. Chem. Lett. 2002, 12, 3551-3555.
22. (a) Smith, A. B., Ill; Levenberg, P. A.; Jerris, P. J.; Scarborough, R. M., Jr.; Wovkulich, P. M. J. Am. Chem. Soc. 1981, 103, 1501-1513.
23. (b) Gogoi, S.; Argade, N. P. Tetrahedron 2006, 62, 2999-3003.
24. (a) Manfredini, S.; Baraldi, P. G.; Bazzanini, R.; Guarneri, M.; Simoni, D.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1994, 37, 2401-2405.
25. (b) Saxena, R.; Singh, V.; Batra, S. Tetrahedron 2004, 60, 10311-10320.
26. Winkler, J. D.; Oh, K.; Asselin. S. M. Org. Lett. 2005, 7, 387-389.
27. (a) Shamshina, J. L.; Snowden, T. S. Tetrahedron Lett. 2007, 48, 3767-3769.
28. (b) Langer, P.; Krummel, T. Chem.-Eur. J. 2001, 7, 1720-1727.
29. (c) Langer, P.; Krummel, T. Chem. Commun. 2000, 967-968.
30. (a) Kato, K.; Nouchi, H.; Ishikura, K.; Takaishi, S.; Motodate, S.; Tanaka, H.; Okudaira, K.; Mochida, T.; Nishigaki, R.; Shigenobu, K.; Akita, H. Tetrahedron 2006, 62, 2545-2554.
31. (b) Villemin, D.; Jaffrès, P.-A.; Hachémi, M. Tetrahedron Lett. 1997, 38, 537-538.
32. (a) Kirsch, S. F.; Binder, J. T.; Liébert, C.; Menz, H. Angew. Chem., Int.Ed. 2006, 45, 5878-5880.
33. (b) Crone, B.; Kirsch, S. F. J. Org. Chem. 2007, 72, 5435-5438.
34. (c) Bunnelle, E. M.; Smith, C. R.; Lee, S. K.; Singaram, S.W.; Rhodes, A. J.; Sarpong, R. Tetrahedron. 2008, 64, 7008-7014.
35. Liu, Y.; Liu, M.; Guo, S.; Tu, H.; Zhou, Y.; Gao, H. Org. Lett. 2006, 8, 3445-3448.
36. (a) Silva, F.; Reiter, M.; Mills-Webb, R.; Sawicki, M.; Klär, D.; Bensel, N.; Wagner, A.; Gouverneur, V. J. Org. Chem. 2006, 71, 8390-8394.
37. (b) Marson, C. M.; Edaan, E.; Morrell, J. M.; Coles, S. J.; Hursthouse, M. B.; Davies, D. T. Chem. Commun. 2007, 2494-2496.
38. Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280-2282.
39. For recent selected reviews, see: (a) Muzart, J. Tetrahedron 2008, 64, 5815-5849.
40. (b) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395-403.
41. (c) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180-3211.
42. (a) Egi, M.; Yamaguchi, Y.; Fujiwara, N.; Akai, S. Org. Lett. 2008, 10, 1867-1870.
43. (b) Egi, M.; Azechi, K.; Akai, S. Org. Lett. 2009, 11, 5002-5005.
44. (a) Saimoto, H.; Shinoda, M.; Matsubara, S.; Oshima, K.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1983, 56, 3088-3092.
45. (b) Kawaguchi, T.; Yasuta, S.; Inoue, Y. Synthesis 1996, 1431-1432.
46. (c) Thomas, A. F.; Damm, H. Tetrahedron Lett. 1986, 27, 505-506.
47. Sakai, T.; Kohda, K.; Tsuboi, S.; Utaka, M.; Takeda, A. Bull. Chem. Soc. Jpn. 1987, 60, 2911-2915.
48. (a) Tokuyama, H.; Miyazaki, T.; Yokoshima, S.; Fukuyama, T. Synlett 2003, 1512-1514.
49. (b) Miyazaki, T.; Han-ya, Y.; Tokuyama, H.; Fukuyama, T. Synktt 2004, 477-480.
50. Ahmad, R.; Khera, R. A.; Villinger, A.; Langer, P. Tetrahedron Lett. 2009, 50, 3020-3022 and references cited therein.
51. The following papers have indicated the bidentate coordination of cationic gold(I) species to both the C≡C triple bond and the lone pair on oxygen atom. Hence, we assumed the formation of intermediate 5 in Scheme 3. (a) Blanc, A.; Tenbrink, K.; Weibel, J.-M.; Pale, P. J. Org. Chem. 2009, 74, 5342-5348.
52. (b) Lopez, S. S.; Engel, D. A.; Dudley, G. B. Synlett 2007, 949-953.
53. Wolff, S.; Agosta, W. C. Can. J. Chem. 1984, 62, 2429-2434.
54. Marion, N.; Ramón, R. S.; Nolan, S. P. J. Am. Chem. Soc. 2009, 131, 448-449.