DDQ-mediated direct Intramolecular-Dehydrogenative-Coupling (IDC): Expeditious approach to the tetracyclic core of ergot alkaloids

Organic Letters

Volumn 15, Issue 10, 2013, Pages 2426-2429

  Bhunia, Subhajit ^a   Ghosh, Santanu ^a   Dey, Dhananjay ^a   Bisai, Alakesh ^a  

^a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH BHOPAL   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84877902361     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400899e     Document Type: Article

References (50)

1. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
2. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 5068
3. McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, 2447
4. Newhouse, T.; Baran, P. S.; Hoffmann, R. W. Chem. Soc. Rev. 2009, 3010
5. Gaich, T.; Baran, P. S. J. Org. Chem. 2010, 75, 4657
6. Hendrickson, J. B. J. Am. Chem. Soc. 1975, 97, 5784
7. Dyker, G., Ed. Handbook of C-H Transformations: Applications in Organic Synthesis, Volume 2; Wiley: New York, 2005.
8. Ashenhurst, J. A. Chem. Soc. Rev. 2010, 540
9. Le Bras, J.; Muzart, J. Chem. Rev. 2011, 111, 1170
10. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780
11. Xu, Y. -C.; Roy, C.; Lebeau, E. Tetrahedron Lett. 1993, 34, 8189
12. Xu, Y. -C.; Lebeau, E.; Attardo, G.; Myers, P. L.; Gillard, J. W. J. Org. Chem. 1994, 59, 4868
13. For metal-free CDC, see: Zhang, Y.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 4242
14. Zhang, Y.; Li, C.-J. Angew. Chem., Int. Ed. 2006, 45, 1949
15. Li, C.-J. Acc. Chem. Res. 2009, 42, 335
16. Yoo, W.-J.; Li, C.-J. Top. Curr. Chem. 2010, 292, 281
17. Millemaggi, A.; Taylor, R. J. K. Eur. J. Org. Chem. 2010, 4527
18. Zhou, F.; Liu, Y. L.; Zhou, J. A. Adv. Synth. Catal. 2010, 352, 1381
19. For synthesis of 2-oxindoles via a Friedel-Crafts alkylations from our group, see: Ghosh, S.; Kinthada, L. K.; Bhunia, S.; Bisai, A. Chem. Commun. 2012, 10132.
20. Jia, Y. X.; Kündig, E. P. Angew. Chem., Int. Ed. 2009, 48, 1636
21. Dey, C.; Kündig, E. P. Chem. Commun. 2012, 3064
22. Dey, C.; Kündig, E. P. Chem. Commun. 2012, 3064
23. Perry, A.; Taylor, R. J. K. Chem. Commun. 2009, 3249
24. Franckevicius, V.; Cuthbertson, J. D.; Pickworth, M.; Pugh, D. S.; Taylor, R. J. K. Org. Lett. 2011, 13, 4264
25. Klein, J. E. M. N.; Perry, A.; Pugh, D. S.; Taylor, R. J. K. Org. Lett. 2010, 12, 3446
26. Moody, C. L.; Franckevicius, V.; Drouhin, P.; Klein, J. E. M. N.; Taylor, R. J. K. Tetrahedron. Lett. 2012, 53, 1897
27. 2-mediated IDC, see: Ghosh, S.; De, S.; Kakde, B. N.; Bhunia, S.; Adhikary, A.; Bisai, A. Org. Lett. 2012, 14, 5864
28. Buckle, D. R. Encyclopaedia of Reagent for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: Chichester, UK, 1995; Vol. 3, p 1699.
29. Patir, S.; Ertürk, E. J. Org. Chem. 2011, 76, 335
30. Ying, B.-P.; Trogden, B. G.; Kohlman, D. T.; Liang, S. X.; Xu, Y.-C. Org. Lett. 2004, 6, 1523
31. Deppermann, N.; Thomanek, H.; Prenzel, A. H. G. P.; Maison, W. J. Org. Chem. 2010, 75, 5994
32. Trost, B. M.; Brennan, M. K. Org. Lett. 2006, 8, 2027
33. Richter, J. M.; Whitefield, B. W.; Maimone, T. J.; Lin, D. W.; Castroviejo, M. P.; Baran, P. S. J. Am. Chem. Soc. 2007, 129, 12857
34. Wang, Y. -H.; Long, C.-L.; Yang, F.-M.; Wang, X.; Sun, Q.-Y.; Wang, H.-S.; Shi, Y.-N.; Tang, G.-H. J. Nat. Prod. 2009, 72, 1151
35. Williams, R. M.; Sanz-Cervera, J. F.; Sancenón, F.; Marco, J. A.; Halligan, K. J. Am. Chem. Soc. 1998, 120, 1090
36. Finefield, J. M.; Frisvad, J. C.; Sherman, D. H.; Williams, R. M. J. Nat. Prod. 2012, 75, 812 and references therein
37. Peters, L.; König, G. M.; Terlau, H.; Wright, A. D. J. Nat. Prod. 2002, 65, 1633
38. Okada, M.; Sato, I.; Cho, S. J.; Dubnau, D.; Sakagami, Y. Tetrahedron 2006, 62, 8907
39. Rochfort, S. J.; Moore, S.; Craft, C.; Martin, N. H.; Van Wagoner, R. M.; Wright, J. L. C. J. Nat. Prod. 2009, 72, 1773
40. For Pd-catalyzed asymmetric prenylations and geranylations, using carbonates as external electrophiles, see: Trost, B. M.; Malhotra, S.; Chan, W. H. J. Am. Chem. Soc. 2011, 133, 7328
41. Inuki, S.; Iwata, A.; Oishi, S.; Fujii, N.; Ohno, H. J. Org. Chem. 2011, 76, 2072
42. Wallwey, C.; Li, S. -M. Chem. Soc. Rev. 2011, 496
43. For synthesis of 3-monosubstituted-2-oxindoles from IDC product of the type ± 4, see: Pugh, D. S.; Klein, J. E. M. N.; Perry, A.; Taylor, R. J. K. Synlett 2010, 934
44. For use of 5-bromo-2-methoxy-6-picolylbromide 22, see: Bisai, V.; Sarpong, R. Org. Lett. 2010, 12, 2551
45. Studer, A.; Bossart, M. In Radicals in Organic Synthesis; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH; Weinheim, 2001; Vol. 2, Chapter 1.4, pp 62-80.
46. Bowman, W. R.; Storey, J. M. D. Chem. Soc. Rev. 2007, 1803
47. De, S.; Ghosh, S.; Bhunia, S.; Sheikh, J. A.; Bisai, A. Org. Lett. 2012, 14, 4466
48. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644
49. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
50. Cacchi, S.; Fabrizi, G. Chem. Rev. 2011, 111, PR215 and references therein