A new approach to 1,4-oxazines and 1,4-oxazepines via base-promoted exo mode cyclization of alkynyl alcohols: Mechanism and DFT studies

Organic Letters

Volumn 14, Issue 12, 2012, Pages 3134-3137

  Vandavasi, Jaya Kishore ^a   Hu, Wan Ping ^a   Chen, Hsing Yin ^a   Senadi, Gopal Chandru ^a   Chen, Chung Yu ^a   Wang, Jeh Jeng ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKYNE; OXAZEPINE DERIVATIVE; OXAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; FOURIER ANALYSIS; STEREOISOMERISM;

ALCOHOLS; ALKYNES; CYCLIZATION; FOURIER ANALYSIS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXAZEPINES; OXAZINES; STEREOISOMERISM;

EID: 84862547253     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301219c     Document Type: Article

References (56)

1. Shimizu, Y. Marine Natural Products; Academic Press: New York, 1978; Vol. 1.
2. Moore, R. E. Marine Natural Products: Chemical and Biological Perspectives; Scheuer, P. J., Ed.; Academic Press: New York, 1978; Vol. 2.
3. Faulkner, D. J. Nat. Prod. Rep. 1986, 3, 1
4. Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897
5. Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75
6. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-735
7. Fukudome, Y.; Naito, H.; Hata, T.; Ura, H. J. Am. Chem. Soc. 2008, 130, 1820-1821
8. Broggini, G.; Beccalli, E. M.; Borsini, E.; Fasana, A.; Zecchi, G. Synlett 2011, 2, 227-230
9. Wang, Z.; Lin, X.; Luck, R. L.; Gibbons, G.; Fang, S. Tetrahedron 2009, 65, 2643-2648
10. Pauff, S. M.; Miller, S. C. Org. Lett. 2011, 13, 6196-6199
11. Zhao, W.; Carreira, E. M. Org. Lett. 2011, 13, 5084-5087
12. Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395-3442
13. Suzuki, S.; Tokunaga, E.; Reddy, D. S.; Matsumoto, T.; Shiro, M. Angew. Chem., Int. Ed. 2012, 51, 4131-4135
14. Ohno, H.; Hamaguchi, H.; Ohata, M.; Kosaka, S.; Tanaka, T. J. Am. Chem. Soc. 2004, 126, 8744-8754
15. Sordo, T.; Campomanes, P.; Diéguez, A.; Rodriguez, F.; Fananas, F. J. J. Am. Chem. Soc. 2005, 127, 944-952
16. Chaudhuri, G.; Kundu, N. G. J. Chem. Soc., Perkin Trans. 1 2000, 775-779
17. Abbiati, G.; Canevari, V.; Caimi, S.; Rossi, E. Tetrahedron Lett. 2005, 46, 7117-7120
18. Yue, D.; Della Cà, N.; Larock, R. C. Org. Lett. 2004, 6, 1581-1584
19. Patil, N. T.; Yamamoto, Y. J. Org. Chem. 2004, 69, 5139-5142
20. Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764-765
21. Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; González, J. M. J. Am. Chem. Soc. 2003, 125, 9028-9029
22. Park, J. H.; Bhilare, S. V.; Youn, S. W. Org. Lett. 2011, 13, 2228-2231
23. Ohno, H.; Kadoh, Y.; Fujii, N.; Tanaka, T. Org. Lett. 2006, 8, 947-950
24. Mukai, C.; Yamashita, H.; Hanaoka, M. Org. Lett. 2001, 3, 3385-3387
25. Mukai, C.; Kobayashi, M.; Kubota, S.; Takahashi, Y.; Kitagaki, S. J. Org. Chem. 2004, 69, 2128-2136
26. Ohno, H.; Kadoh, Y.; Fujii, N.; Tanaka, T. Org. Lett. 2006, 8, 947-950
27. Kitagaki, S.; Teramoto, S.; Mukai, C. Org. Lett. 2007, 9, 2549-2552
28. Mukai, C.; Ukon, R.; Kuroda, N. Tetrahedron Lett. 2003, 44, 1583-1586
29. Mukai, C.; Kuroda, N.; Ukon, R.; Itoh, R. J. Org. Chem. 2005, 70, 6282-6290
30. Kitagaki, S.; Shibata, D.; Mukai, C. Tetrahedron Lett. 2007, 48, 1735-1738
31. Kitagaki, S.; Teramoto, S.; Ohta, Y.; Kobayashi, H.; Takabe, M.; Mukai, C. Tetrahedron 2010, 66, 3687-3694
32. Yu, X.; Seo, S. Y.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 7244-7245
33. Dzudza, A.; Marks, T. J. Chem.-Eur. J. 2010, 16, 3403-3422
34. Seo, S.; Yu, X.; Marks, T. J. J. Am. Chem. Soc. 2009, 131, 263-276
35. Barluenga, J.; Dieguez, A.; Rodriguez, F.; Fananas, F. J.; Sordo, T.; Campomanes, P. Chem.-Eur. J. 2005, 11, 5735-5741
36. Ruettinger, R.; Leutzow, J.; Wilsdorf, M.; Wilckens, K.; Czekelius, C. Org. Lett. 2011, 13, 224-227
37. Pale, P.; Chuche, J. Eur. J. Org. Chem. 2000, 6, 1019-1026
38. Praveen, C.; Iyyappan, C.; Perumal, P. T. Tetrahedron Lett. 2010, 51, 4767-4771
39. Davies, S. G.; Roberts, P. M.; Stephenson, P. T.; Thomson, J. E. Tetrahedron Lett. 2009, 50, 3509-3512
40. Hashmi, A. S. K.; Haufe, P.; Schmid, C.; Nass, A. R.; Frey, W. Chem.-Eur. J. 2006, 12, 5376-5382
41. Cadierno, V.; Diez, J.; Gimeno, J.; Nebra, N. J. Org. Chem. 2008, 73, 5852-5858
42. Riediker, M.; Schwartz, J. J. Am. Chem. Soc. 1982, 104, 5842-5844
43. Ramana, C. V.; Induvadana, B.; Srinivas, B.; Yadagiri, K.; Deshmukh, M. N.; Gonnade, R. G. Tetrahedron 2009, 65, 9819-9832
44. Li, H. J.; Guillot, R.; Gandon, V. J. Org. Chem. 2010, 75, 8435-8449
45. Barluenga, J.; Fernandez, A.; Satrustegui, A.; Dieguez, A.; Rodriguez, F.; Fananas, F. Chem.-Eur. J. 2008, 14, 4153-4156
46. Wang, J. Z.; Lin, X.; Luck, R. L.; Gibbons, G.; Fang, S. Tetrahedron 2009, 65, 2643-2648
47. Lysek, R.; Furman, B.; Kaluza, Z.; Frelek, J.; Suwinska, K.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron: Asymmetry 2000, 11, 3131-3150
48. Pettigrew, J. D.; Wilson, P. D. Org. Lett. 2006, 8, 1427-1429
49. Fernandez, A. V.; Yebra, C. G.; Varela, J. A.; Esteruelas, M. A.; Saa, C. Angew. Chem., Int. Ed. 2010, 49, 4278-4281
50. Alcazar, E.; Pletcher, J. M.; McDonald, F. E. Org. Lett. 2004, 6, 3877-3880
51. McDonald, F.; Reddy, K. S. Angew. Chem., Int. Ed. 2001, 40, 3653-3655
52. Liu, F. N.; Su, F. H.; Wen, T. B.; Sung, H.-Y.; Williams, I. D.; Jia, G. Chem.-Eur. J. 2010, 16, 7889-7897
53. Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 2003, 125, 7482-7483
54. McDonald, F. E.; Gleason, M. M. J. Am. Chem. Soc. 1996, 118, 6648-6659
55. Chen, X.; Hortelano, E. R.; Eliel, E. L. J. Am. Chem. Soc. 1990, 112, 6130-6131
56. Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778-1784