Anodic coupling reactions: A sequential cyclization route to the arteannuin ring skeleton

Organic Letters

Volumn 9, Issue 22, 2007, Pages 4599-4602

  Wu, Honghui ^a   Moeller, Kevin D ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTEMISININ; ARTEMISININ DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

ARTEMISININS; CYCLIZATION; MOLECULAR STRUCTURE;

EID: 35948984444     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702118n     Document Type: Article

References (33)

1. For a recent review of the use of electrochemistry in synthesis, see: Sperry, J. B.; Wright, D. L. Chem. Soc. Rev. 2006, 35, 605.
2. For general references specifically dealing with oxidative enol ether-furan coupling reactions, see: (a) Moeller, K. D.; New, D. G. Tetrahedron Lett. 1994, 35, 2857.
3. (b) Moeller, K. D.; Tesfai, Z. J. Electrochem. Soc. Jpn. (Denki Kagaku) 1994, 62, 1115.
4. (c) New, D. G.; Tesfai, Z.; Moeller, K. D. J. Org. Chem. 1996, 61, 1578-1598.
5. (d) Whitehead, C. R.; Sessions, E. H.; Ghiviriga, I.; Wright D. L. Org. Lett. 2002, 4, 3763.
6. (e) Sperry, J. B.; Whitehead, C. R.; Ghiviriga, I.; Walczak, R. M.; Wright, D. L. J. Org. Chem. 2004, 69, 3726.
7. (f) Sperry, J. B.; Wright, D. L. J. Am. Chem. Soc. 2005, 127, 8034.
8. (g) Sperry, J. B.; Cnstanzo, J. R.; Jasinski, J.; Butcher, R. J.; Wright, D. L. Tetrahedron Lett. 2005, 46, 2789.
9. (h) Sperry, J. B.; Wright, D. L. Tetrahedron 2006, 62, 6551.
10. (a) Mihelcic, J.; Moeller, K. D. J. Am. Chem. Soc. 2003, 125, 36.
11. (b) Mihelcic, J.; Moeller, K. D. J. Am. Chem. Soc. 2004, 126, 9106.
12. Wright, D. L.; Whitehead, C. R.; Sessions, E. H.; Ghiviriga, I.; Frey, D. A. Org. Lett. 1999, 1, 1535.
13. (a) Hughes, C. C.; Miller, A. K.; Trauner, D. Org. Lett. 2005, 7, 3425.
14. (b) Miller, A. K.; Hughes, C. C.; Kennedy-Smith, J. J.; Gradl, S. N.; Trauner, D. J. Am. Chem. Soc. 2006, 128, 17057.
15. For recent work examining the reactivity of the radical cation intermediates involved in anodic olefin coupling reactions, see: Huang, Y.; Moeller, K. D. Tetrahedron 2006, 62, 6536 and references therein.
16. For initial characterization studies, see: Sy, L.-K.; Borwn, G. D.; Haynes, R. Tetrahedron 1998, 54, 4345.
17. For more recent structural and synthetic studies, see: (b) Sy, L.-K.; Cheung, K.-K.; Zhu, N.-Y.; Brown, G. D. Tetrahedron 2001, 57, 8481.
18. (c) Sy, L.-K.; Zhu, N.-Y.; Brown, G. D. Tetrahedron 2001, 57, 8495.
19. For previous synthetic approaches to the arteanniuns and related molecules, see: (a) Bariault, L.; Deon, D. H. Org. Lett. 2001, 3, 1925.
20. (b) Sy, L.-K.; Ngo, K.-S.; Brown, G. D. Tetrahedron 1999, 55, 15127.
21. (c) Nowak, D. M.; Lansbury, P. T. Tetrahedron 1998, 54, 319.
22. (d) Schwaebe, M.; Little, R. D. J. Org. Chem. 1996, 61, 3240.
23. (e) Jefford, C. W.; Velarde, J.; Bernardinelli, G. Tetrahedron Lett. 1989, 30, 4485.
24. (f) Zhou, W. S.; Zhang, L.; Fan, Z. C.; Xu, X. X. Tetrahedron 1986, 42, 4437.
25. (g) Lansbury, P. T.; Mojica, C. A. Tetrahedron Lett. 1986, 27, 3967.
26. (h) Xu, X.; Zhu, J.; Huang, D.; Xhou, W. Tetrahedron 1986, 42, 819.
27. For a previous anodic olefin coupling reaction utilizing an endocyclic enol ether and a simple olefin trapping group, see: Hudson, C. M.; Marzabadi, M. R.; Moeller, K. D.; New, D. G. J. Am. Chem. Soc. 1991, 113, 7372.
28. For related electrochemical cyclizations forming five-membered rings through the dearomatization of a furan, see: Sperry, J. B.; Ghiviriga, I.; Wright, D. L. Chem. Commun. 2006, 2, 194.
29. For radical cyclization reactions involving furan rings, see: (a) Parsons, P. J.; Penverne, M.; Pinto, I. L. Synlett 1994, 721.
30. (b) Demircan, A.; Parsons, P. J. Eur. J. Org. Chem. 2003, 1729.
31. 4 in acetonitrile electrolyte solution, and a 0.025 M concentration of substrate.
32. Petasis, N. A. Transition Metals for Organic Synthesis, 2nd ed.; Wiley: New York, 2004; Vol. 1, p 427.
33. Horner, J.; Taxil, E.; Newcomb, M. J. Am. Chem. Soc. 2002, 124, 5402.