Stereoselective synthesis of oxa- and aza-angular triquinanes using tandem radical cyclization to vinylogous carbonates and carbamates

Organic Letters

Volumn 14, Issue 21, 2012, Pages 5476-5479

  Gharpure, Santosh J ^a,b   Niranjana, P ^a   Porwal, Suheel K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

^b INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; CARBONIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; SESQUITERPENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; SYNTHESIS;

AZA COMPOUNDS; CARBAMATES; CARBONATES; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; MOLECULAR STRUCTURE; SESQUITERPENES;

EID: 84868351634     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302557a     Document Type: Article

References (60)

1. Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671
2. Singh, V.; Thomas, B. Tetrahedron 1998, 54, 3647
3. Marchand, A. P. Synlett 1991, 73
4. Yadav, J. S.; Kumar, P. T. K.; Gadgil, V. R. Tetrahedron Lett. 1992, 33, 3687
5. Woltering, T. J.; Hoffmann, H. M. R. Tetrahedron 1995, 51, 7389
6. Singh, V.; Alam, S. Q. Bioorg. Med. Chem. Lett. 2000, 10, 2517
7. Ader, T. A.; Champey, C. A.; Kuznetsova, L. V.; Li, T.; Lim, Y.-H.; Rucando, D.; Sieburth, S. McN. Org. Lett. 2001, 3, 2165
8. Gurjar, M. K.; Ravindranadh, S. V.; Kumar, P. Chem. Commun. 2001, 917
9. Singh, V.; Alam, S. Q.; Praveena, G. D. Tetrahedron 2002, 58, 9729
10. Kaliappan, K. P.; Nandurdikar, R. S. Chem. Commun. 2004, 2506
11. Kaliappan, K. P.; Nandurdikar, R. S.; Shaikh, M. M. Tetrahedron 2006, 62, 5064
12. Ramakrishna, K.; Kaliappan, K. P. Synlett 2011, 2580
13. Liao, J.-H.; Maulide, N.; Augustyns, B.; Marko, I. E. Org. Biomol. Chem. 2006, 4, 1464
14. Mascal, M.; Hafezi, N.; Meher, N. K.; Fettinger, J. C. J. Am. Chem. Soc. 2008, 130, 13532
15. Clive, D. L. J.; Cole, D. C.; Tao, Y. J. Org. Chem. 1994, 59, 1396
16. Hext, N. M.; Hansen, J.; Blake, A. J.; Hibbs, D. E.; Hursthouse, M. B.; Shishkin, O. V.; Mascal, M. J. Org. Chem. 1998, 63, 6016
17. Li, Y.; Meng, Y.; Meng, X.; Li, Z. Tetrahedron 2011, 67, 4002
18. Zancanella, M. A.; Romo, D. Org. Lett. 2008, 10, 3685
19. Kudryavtsev, K. V. Heterocycles 2011, 83, 323
20. Bandaru, A.; Kaliappan, K. P. Synlett 2012, 1473
21. Huang, J.-M.; Yokoyama, R.; Yang, C.-S.; Fukuyama, Y. Tetrahedron Lett. 2000, 41, 6111
22. Huang, J.-M.; Yang, C.-S.; Tanaka, M.; Fukuyama, Y. Tetrahedron 2001, 57, 4691
23. Lee, E.; Tae, J. S.; Lee, C.; Park, M. C. Tetrahedron Lett. 1993, 34, 4831
24. Ko, H. M.; Lee, C. W.; Kwon, H. K.; Chung, H. S.; Choi, S. Y.; Chung, Y. K.; Lee, E. Angew. Chem., Int. Ed. 2009, 48, 2364
25. Matsuo, G.; Kadohama, H.; Nakata, T. Chem. Lett. 2002, 31, 148
26. Evans, P. A.; Murthy, V. S.; Roseman, J. D.; Rheingold, A. L. Angew. Chem., Int. Ed. 1999, 38, 3175
27. Evans, P. A.; Roseman, J. D. J. Org. Chem. 1996, 61, 2252
28. Leeuwenburgh, M. A.; Litjens, R. E. J. N.; Codée, J. D. C.; Overkleeft, H. S.; Van der Marel, G. A.; Van Boom, J. H. Org. Lett. 2000, 2, 1275
29. Sibi, M. P.; Patil, K.; Rheault, T. R. Eur. J. Org. Chem. 2004, 372
30. Pandey, G.; Hajra, S.; Ghorai, M. K.; Ravi Kumar, K. J. Org. Chem. 1997, 62, 5966
31. Chakraborty, T. K.; Samanta, R.; Ravikumar, K. Tetrahedron Lett. 2007, 48, 6389 and references therein
32. Navarro-Vazquez, A.; Garcia, A.; Dominguez, D. J. Org. Chem. 2002, 67, 3213
33. Berlin, S.; Ericsson, C.; Engman, L. J. Org. Chem. 2003, 68, 8386
34. Chakraborty, T. K.; Samanta, R.; Roy, S.; Sridhar, B. Tetrahedron Lett. 2009, 50, 3306
35. Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S.; Chung, C. K. Tetrahedron Lett. 1995, 36, 417
36. Macdonald, S. J. F.; Mills, K.; Spooner, J. E.; Upton, R. J.; Dowle, M. D. J. Chem. Soc., Perkin Trans. 1 1998, 3931
37. Gharpure, S. J.; Reddy, S. R. B. Org. Lett. 2009, 11, 2519
38. Gharpure, S. J.; Shukla, M. K.; Vijayasree, U. Org. Lett. 2009, 11, 5466
39. Gharpure, S. J.; Reddy, S. R. B. Tetrahedron Lett. 2010, 51, 6093
40. Gharpure, S. J.; Sathiyanarayanan, A. M. Chem. Commun. 2011, 47, 3625
41. Gharpure, S. J.; Nanda, L. N.; Shukla, M. K. Eur. J. Org. Chem. 2011, 6632
42. Gharpure, S. J.; Prasath, V. J. Chem. Sci. 2011, 123, 943
43. Gharpure, S. J.; Vijayasree, U.; Reddy, S. R. B. Org. Biomol. Chem. 2012, 10, 1735
44. Gharpure, S. J.; Porwal, S. K. Synlett 2008, 242
45. Gharpure, S. J.; Porwal, S. K. Tetrahedron Lett. 2009, 50, 7162
46. McCarroll, A. J.; Walton, J. C. Angew. Chem., Int. Ed. 2001, 40, 2224
47. Malacria, M. Chem. Rev. 1996, 96, 289
48. Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177
49. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001
50. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811
51. Guerra, K. P.; Afonso, C. A. M. Tetrahedron 2011, 67, 2562
52. Luche, J. L. J. Am. Chem. Soc. 1978, 100, 2226
53. Gemal, A. L.; Luche, J. L. J. Am. Chem. Soc. 1981, 103, 5454
54. Kumara Swamy, K. C.; Bhuvan Kumar, N. N.; Balaraman, E.; Pavan Kumar, K. V. P. Chem. Rev. 2009, 109, 2551
55. But, T. Y. S.; Toy, P. H. Chem. Asian J. 2007, 2, 1340
56. Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003
57. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
58. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209
59. Evans, P. A.; Lai, K. W.; Zhang, H. R.; Huffman, J. C. Chem. Commun. 2006, 844
60. Evans, P. A.; Manangan, T.; Rheingold, A. L. J. Am. Chem. Soc. 2000, 122, 11009 and refrences cited therein