Marrying iterative synthesis to cascading radical cyclization: 6-endo/5-exo radical cascade across bis-vinyl ethers

Organic Letters

Volumn 13, Issue 20, 2011, Pages 5552-5555

  Davies, Katherine A ^a   Wulff, Jeremy E ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL; VINYL DERIVATIVE; VINYL ETHER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM;

COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; FREE RADICALS; MOLECULAR STRUCTURE; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 80054679907     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202286q     Document Type: Article

References (46)

1. Merrifield, R. B. Angew. Chem., Int. Ed. Engl. 1985, 24, 799-810
2. Caruthers, M. H. Science 1985, 230, 281-285
3. Atherton, E.; Sheppard, R. C. Solid-Phase Peptide Synthesis: A Practical Approach; Oxford Univ. Press: Oxford, U.K., 1989.
4. Weishaupt, M.; Eller, S.; Seeberger, P. H. Methods Enzymol. 2010, 478, 463-484
5. Sears, P.; Wong, C.-H. Science 2001, 291, 2344-2350
6. Wong, C.-H. J. Org. Chem. 2005, 70, 4219-4225
7. Paterson, I.; Scott, J. P. J. Chem. Soc., Perkin Trans. 1 1999, 1003-1014
8. Kesavan, S.; Su, Q.; Shao, J.; Porco, J. A., Jr.; Panek, J. S. Org. Lett. 2005, 7, 4435-4438
9. Paterson, I.; Gottschling, D.; Menche, D. Chem. Commun. 2005, 3568-3570
10. Evans, P. A.; Roseman, J. D.; Garber, L. T. J. Org. Chem. 1996, 61, 4880-4881
11. Marmsäter, F. P.; West, F. G. J. Am. Chem. Soc. 2001, 123, 5144-5145
12. Kadota, I.; Takamura, H.; Sato, K.; Yamamoto, Y. J. Org. Chem. 2002, 67, 3494-3498
13. Trost, B. M.; Frederiksen, M. U.; Rudd, M. T. Angew. Chem., Int. Ed. 2005, 44, 6630-6666
14. Simpson, G. L.; Heffron, T. P.; Merino, E.; Jamison, T. F. J. Am. Chem. Soc. 2006, 128, 1056-1057
15. For a recent review, see: Snyder, S. A.; ElSohly, A. M.; Kontes, F. Nat. Prod. Rep. 2011, 28, 897-924
16. Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2007, 129, 6716-6717
17. Noguchi, H.; Hojo, K.; Suginome, M. J. Am. Chem. Soc. 2007, 129, 758-759
18. Lee, S. J.; Anderson, T. M.; Burke, M. D. Angew. Chem., Int. Ed. 2010, 49, 8860-8863
19. Gillis, E. P.; Burke, M. D. Aldrichimica Acta 2009, 42, 17-27
20. Manabe, K.; Ohba, M.; Matsushima, Y. Org. Lett. 2011, 13, 2436-2439
21. Nicolaou, K. C.; Chen, J. S. Chem. Soc. Rev. 2009, 38, 2993-3009
22. Touré, B. B.; Hall, D. G. Chem. Rev. 2009, 109, 4439-4486
23. Bur, S. K.; Padwa, A. Adv. Heterocycl. Chem. 2007, 94, 1-105
24. Inanaga, J.; Baba, Y.; Hanamoto, T. Chem. Lett. 1993, 241-244
25. A similar sequence of reactions was recently used by our group to prepare a family of juvenile hormone mimics; see: Davies, K. A.; Kou, K. G. M.; Wulff, J. E. Tetrahedron Lett. 2011, 52, 2302-2305
26. Lubineau, A.; Augé, J.; Bellanger, N.; Caillebourdin, S. J. Chem. Soc., Perkin Trans. 1 1992, 1631-1636
27. Krompiec, S.; Kuźnik, N.; Urbala, M.; Rzepa, J. J. Mol. Catal. A: Chem. 2006, 248, 198-209. Also see ref 11
28. Handa, S.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1999, 843-845
29. Handa, S.; Nair, P. S.; Pattenden, G. Helv. Chim. Acta 2000, 83, 2629-2643
30. Munt, S. P.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 480-482
31. Maguire, R. J.; Munt, S. P.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1998, 2853-2864
32. Less substituted 1,5-dienes (where both alkenes were disubstituted) were reported to engage in tandem 6- endo-trig /5- exo-trig cyclization, but the presence of additional substituents favored the 6- endo pathway; see: Batsanov, A.; Chen, L.; Gill, G. B.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1996, 45-55
33. Fleming, I. Molecular Orbitals and Organic Chemical Reactions; John Wiley & Sons: West Sussex, U.K., 2010; pp 369-400.
34. Lee, E. Pure Appl. Chem. 2005, 77, 2073-2081
35. 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, 1275-1277
36. Anomeric radicals generally react through axial approach of the radical acceptor; see for example: Abe, H.; Shuto, S.; Matsuda, A. J. Am. Chem. Soc. 2001, 123, 11870-11882 and references therein.
37. Shibano, M.; Okuno, A.; Taniguchi, M.; Baba, K.; Wang, N.-H. J. Nat. Prod. 2005, 68, 1445-1449
38. Li, C.-Y.; Wu, T.-S. J. Nat. Prod. 2002, 65, 1452-1456
39. Seaforth, C. E.; Mohammed, S.; Maxwell, A.; Tinto, W. F.; Reynolds, W. F. Tetrahedron Lett. 1992, 33, 4111-4114
40. Oulad-Ali, A.; Guillaume, D.; Jiang, Y.; Weniger, B.; Anton, R. Nat. Prod. Lett. 1993, 2, 203-207
41. Krohn, K.; Biele, C.; Drogies, K.-H.; Steingröver, K.; Aust, H.-J.; Draeger, S.; Schulz, B. Eur. J. Org. Chem. 2002, 2331-2336
42. Qin, S.; Krohn, K.; Flörke, U.; Schulz, B.; Draeger, S.; Pescitelli, G.; Salvadori, P.; Antus, S.; Kurtán, T. Eur. J. Org. Chem. 2009, 3279-3284
43. Gao, X.; Nakadai, M.; Snider, B. B. Org. Lett. 2003, 5, 451-454 and references therein.
44. Stewart, A. M.; Meier, K.; Schulz, B.; Steinert, M.; Snider, B. B. J. Org. Chem. 2010, 75, 6057-6060
45. Ghosh, A. K.; Chapsal, B. D.; Baldridge, A.; Steffey, M. P.; Walters, D. E.; Koh, Y.; Amano, M.; Mitsuya, H. J. Med. Chem. 2011, 54, 622-634
46. Fathi, A. R.; Krautheim, A.; Kaap, S.; Eger, K.; Steinfelder, H. J. Bioorg. Med. Chem. Lett. 2000, 10, 1605-1608