Construction of carbo- And heterocycles using radical relay cyclizations initiated by alkoxy radicals

Organic Letters

Volumn 11, Issue 9, 2009, Pages 2019-2022

  Zhu, Hai ^a   Wickenden, Jason G ^a   Campbell, Natalie E ^a   Leung, Joe C T ^a   Johnson, Kayli M ^a   Sammis, Glenn M ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIDINOLIDE K; FURAN DERIVATIVE; MACROLIDE; TETRAHYDROFURAN;

ANIMAL; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; DINOFLAGELLATE; STEREOISOMERISM; SYNTHESIS;

ANIMALS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; DINOFLAGELLIDA; FURANS; MACROLIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 65549100154     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900481e     Document Type: Article

References (58)

1. For recent advances, see: (a) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330-7331.
2. (b) Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192-7193.
3. (c) Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 7460-7461.
4. (d) Wakui, H.; Kawasaki, S.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2004, 126, 8658-8659.
5. (e) Campeau, L.-C.; Parisien, M.; Leblanc, M.; Fagnou, K. J. Am. Chem. Soc. 2004, 126, 9186-9187.
6. (f) Orito, K.; Horibata, A.; Nakamura, T.; Ushito, H.; Nagasaki, H.; Yuguchi, M.; Yamashita, S.; Tokuda, M. J. Am. Chem. Soc. 2004, 126, 14342-14343.
7. For reviews, see: (a) Davies, H. M.; Manning, J. R. Nature (London) 2008, 451, 417-424.
8. (b) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101.
9. (c) Davies, H. M.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861-2904.
10. (d) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1770.
11. For reviews on carbon-radical cyclizations, see: (a) Ramaiah, M. Tetrahedron 1987, 43, 3541-3676.
12. (b) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, Chapter 4.1, pp 715-777.
13. (c) Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. In Organic Reactions; Paquette, L., Eds.; John Wiley & Sons, Inc.: New York, 1996; Vol. 48, Chapter 2, pp 303-856.
14. (d) Gansauer, A.; Bluhm, H. Chem. Rev. 2000, 100, 2771-2788.
15. (e) Curran, D. P. Synthesis 1988, 417-439.
16. (f) Curran, D. P. Synthesis 1988, 489-513.
17. 1,5-Hydrogen abstractions with subsequent functionalizations have been studied extensively by Breslow. For a review, see: Breslow, R. Acc. Chem. Res. 1980, 13, 170-177.
18. For early reports on the use of vinyl radicals for radical relay cyclizations, see: (a) Heiba, E. I.; Dessau, R. M. J. Am. Chem. Soc. 1967, 89, 3772-3777.
19. (b) Chenera, B.; Chuang, C.-P.; Hart, D. J.; Hsu, L.-Y. J. Org. Chem. 1985, 50, 5409-5410.
20. (c) Bennett, S. M.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1986, 878-880.
21. (d) Lathbury, D. C.; Parsons, P. J.; Pinto, I. J. Chem. Soc., Chem. Commun. 1988, 81-82.
22. Curran, D. P.; Kim, D.; Liu, H. T.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900-5902.
23. (e) Borthwick, A. D.; Caddick, S.; Parsons, P. J. Tetrahedron Lett. 1990, 31, 6911-6914.
24. For early reports on the use of aryl radicals for radical relay cyclizations, see: (a) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896-898.
25. (b) Curran, D. P.; Abraham, A. C.; Liu, H. J. Org. Chem. 1991, 56, 4335-4337.
26. (c) Beckwith, A. L. J.; O'Shea, D. M.; Gerba, S.; Westwood, S. W. J. Chem. Soc., Chem. Commun. 1987, 666-667.
27. For a recent review, see: Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
28. For early reports, see: (a) Cainelli, G.; Mihaiovic, M. L.; Arigoni, D.; Jeger, O. Helv. Chim. Acta 1959, 42, 1124-1127.
29. (b) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1960, 82, 2640-2641.
30. (c) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1960, 82, 2641-2641.
31. For recent reviews and representative examples, see: (a) Čeković, Ž. Serb. J. Chem. Soc. 2005, 70, 287-318.
32. (b) Čeković, Ž. Tetrahedron 2003, 59, 8073-8090.
33. (c) Hartung, J.; Gottwald, T.; Spehar, K. Synthesis 2002, 1469-1498.
34. (d) Petrović, G.; Čeković, Ž. Tetrahedron 1999, 55,1377-1390.
35. (e) Majetich, G.; Wheless, K. Tetrahedron 1995, 51, 7095-7129.
36. (f) Petrović, G.; Saiǐć, R. N.; Č eković, Ž. Tetrahedron 2003, 59, J87-196v
37. For intermolecular examples, see: (a) Petrović, G.; Čeković, Ž. Tetrahedron Lett. 1997, 38, 627-630.
38. (b) Tsunoi, S; Ryu, I.; Okuda, T.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1998, 120, 8692-8701.
39. (c) Martín, A.; Pérez-Martín, I.; Quintanal, L. M.; Suárez, E. Tetrahedron Lett. 2008, 49, 5179-5181.
40. For intramolecular examples, see: (a) Čeković, Ž.; Ilijev, D. Tetrahderon Lett. 1988, 29, 1441-1444.
41. (b) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181-5183.
42. (c) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439-3442.
43. (d) Moman, E.; Nicoletti, D.; Mourino, A. Org. Lett. 2006, 8, 1249-1251.
44. For a single example of a radical relay cyclization initiated by a nitrogen-centered radical, see: Kim, S.; Yeon, K. M.; Yoon, K. S. Tetrahedron Lett. 1997, 38, 3919-3922.
45. The cyclized product was obtained in 50% yield. The diastereomeric ratio was not reported. See ref 11b.
46. (a) Kim, S.; Lee, T. A.; Song, Y. Synlett 1998, 471-472.
47. (b) Okada, K.; Okamoto, K.; Oda, M. J. Am. Chem. Soc. 1998, 110, 8736-8738.
48. (c) Barton, D. H. R.; Blundell, P.; Jaszberenyl, J. C. Tetrahedron Lett. 1989, 30, 2341-2344.
49. For the development of tris(trimethylsilyl)silane as a radical reducing agent, see: Chatgilialoglu, C.; Griller, D.; Lesage, M. J. Org. Chem. 1988, 53, 3641-3642.
50. For the use of tris(trimethylsilyl)silane in the generation of oxygen- centered radicals, see ref 14a.
51. The E/Z ratio is 3:1. See the Supporting Information for details.
52. For representative reviews, see: (a) Rupprecht, J. K.; Hui, Y.-H.; McLaughlin, J. L. J. Nat. Prod. 1990,53, 237-278.
53. (b) Kobayashi, J.; Tsuda, M. Nat. Prod. Rep. 2004, 21, 77-93.
54. Ishibashi, M.; Sato, M.; Kobayashi, J. J. Org. Chem. 1993, 58, 6928-6929.
55. For a synthesis of (+)-amphidinolide K, see: Williams, D. R.; Meyer, K. G. J. Am. Chem. Soc. 2001, 123, 765-766.
56. For a synthesis of (-)-amphidinolide K, see: 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, 2364-2366.
57. For synthetic efforts toward the synthesis of ( - )-amphidinolide K, see: (a) Williams, D. R.; Meyer, K. G. Org. Lett. 1999, 1, 1303-1305.
58. (b) Andreou, T.; Costa, A. M.; Esteban, L.; Gonzalez, L.; Mas, G.; Vilarrasa, J. Org. Lett. 2005, 7, 4083-4086.