Synthesis of 5-hydroxycyclopent-2-Enones from allenyl vinyl ketones via an interrupted Nazarov cyclization

Organic Letters

Volumn 11, Issue 6, 2009, Pages 1229-1231

  Marx, Vanessa M ^a   Burnell, D Jean ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 64349107003     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900029d     Document Type: Article

References (45)

1. Reviews: (a) Pellissier, H. Tetrahedron 2005, 61, 6479-6517.
2. (b) Frontier, A. J.; Collison, C. Tetrahedron 2005, 61, 7577-7606.
3. (c) Tius, M. A. Eur. J. Org. Chem. 2005, 2193-2206.
4. (a) He, W.; Sun, X.; Frontier, A. J. J. Am. Chem. Soc. 2003, 125, 14278-14279.
5. (b) He, W.; Herrick, I. R.; Atesin, T. A.; Caruana, P. A.; Kellenberger, C. A.; Frontier, A. J. J. Am. Chem. Soc. 2008, 130, 1003-1011.
6. (a) Bee, C.; Leclerc, E.; Tius, M. A. Org. Lett. 2003, 5, 4927-4930.
7. (b) Liang, G.; Gradl, S. N.; Trauner, D. Org. Lett. 2003, 5, 4931-4934.
8. (c) Liang, G.; Trauner, D. J. Am. Chem. Soc. 2004, 126, 9544-9545.
9. (d) Batson, W. A.; Sethumadhavan, D.; Tius, M. A. Org. Lett. 2005, 7, 2771-2774.
10. (e) Prandi, C.; Deagostino, A.; Venturello, P.; Occhiato, E. G. Org. Lett. 2005, 7, 4345-4348.
11. (f) Janka, M.; He, W.; Haedicke, I. E.; Fronczek, F. R.; Frontier, A. J.; Eisenberg, R. J. Am. Chem. Soc. 2006, 128, 5312-5313.
12. (g) Williams, D. R.; Robinson, L. A.; Nevill, C. R.; Reddy, J. P. Angew. Chem., Int. Ed. 2007, 46, 915-918.
13. (h) Rueping, M.; Ieawsuwan, W.; Antonchick, A. P.; Nachtsheim, B. J. Angew. Chem., Int. Ed. 2007, 46, 2097-2100.
14. (i) Amere, M.; Blanchet, J.; Lasne, M.-C.; Rouden, J. Tetrahedron Lett. 2008, 49, 2541-2545.
15. Two computational studies of Nazarov cyclizations confirm the facilitation of Nazarov cyclization by an a oxygen substituent: (a) Cavalli, A.; Masetti, M.; Recanatini, M.; Prandi, C; Guarna, A.; Occhiato, E. G. Chem. Eur. J. 2006, 12, 2836-2845.
16. (b) Polo, V.; Andrés, J. J. Chem. Theory Comput. 2007, 3, 816-823.
17. Tius, M. A. Acc. Chem. Res. 2003, 36, 284-290, and references therein.
18. (a) Leclerc, E.; Tius, M. A. Org. Lett. 2003, 5, 1171-1174.
19. (b) Forest, J.; Bee, C.; Cordaro, F.; Tius, M. A. Org. Lett. 2003, 5, 4069-4072.
20. (c) delos Santos, D. B.; Banaag, A. R.; Tius, M. A. Org. Lett. 2006, 8, 2579-2582.
21. (d) Banaag, A. R.; Tius, M. A. J. Am. Chem. Soc. 2007, 129, 5328-5329.
22. (e) Banaag, A. R.; Tius, M. A. J. Org. Chem. 2008, 73, 8133-8141.
23. (a) Dhoro, F.; Tius, M. A. J. Am. Chem. Soc. 2005, 127, 12472-12473.
24. (b) Dhoro, F.; Kristensen, T. E.; Stockmann, V.; Yap, G. P. A.; Tius, M. A. J. Am. Chem. Soc. 2007, 129, 7256-7257.
25. (c) Basak, A. K.; Tius, M. A. Org. Lett. 2008, 10, 4073-4076.
26. Hashmi, A. S.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Tetrahedron Lett. 1998, 39, 7491-7494.
27. This use of an allene in a Nazarov cyclization was preceded by the following report, in which an oxygen-substituted allene underwent Nazarov cyclization during workup: Tius, M. A.; Kwok, C.-K.; Gu, X.; Zhao, C. Synth. Commun. 1994, 24, 871-885.
28. (a) Shoppee, C. W.; Cooke, B. J. A. J. Chem. Soc., Perkin Trans. 1 1972, 2271, 2276.
29. (b) Binet du Jassonneix, C. Bull. Soc. Chim. Fr. 2 1974, 758-769.
30. (c) Hirano, S.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1974, 1429-1430.
31. (d) de Lera, A. R.; Rey, J. G.; Hrovat, D.; Iglesias, B.; López, S. Tetrahedron Lett. 1997, 38, 7425-7428.
32. (e) Nair, V.; Bindu, S.; Sreekumar, V.; Chiaroni, A. Org. Lett. 2002, 4, 2821-2823.
33. Photochemical Nazarov cyclizations involve trapping of the intermediate by solvent: Habermas, K. L.; Denmark, S. E.; Jones, T. K. Org. React. 1994, 45, 1-158, and references therein.
34. Recent examples by West: (a) Browder, C. C.; Marmsäter, F. P.; West, F. G. Can. J. Chem. 2004, 82, 375-385.
35. (b) White, T. D.; West, F. G. Tetrahedron Lett. 2005, 46, 5629-5632.
36. (c) Giese, S.; Mazzola, R. D., Jr.; Amann, C. M.; Arif, A. M.; West, F. G. Angew. Chem., Int. Ed. 2005, 44, 6546-6549.
37. (d) Grant, T. N.; West, F. G. J. Am. Chem. Soc. 2006, 128, 9348-9349.
38. (e) Rostami, A.; Wang, Y.; Arif, A. M.; McDonald, R.; West, F. G. Org. Lett. 2007, 9, 703-706.
39. (f) Mahmoud, B.; West, F. G Tetrahedron Lett. 2007, 48, 2091-5094.
40. (g) Grant, T. G.; West, F. G. Org. Lett. 2007, 9, 3789-3792.
41. (h) Rieder, C. J.; Fradette, R. J.; West, F. G. Chem. Commun. 2008, 1572-1574.
42. (a) Isaac, M. B.; Chan, T.-H. J. Chem. Soc., Chem. Commun. 1995, 1003-1004.
43. (b) Alcaide, B.; Almendros, P.; Rodrígues-Acebes, R. J. Org. Chem. 2005, 70, 3198-3204.
44. Yields with indium seem to be better than via the tin compound. For instance, 4d synthesized via the propargyltin was produced in 21% yield, as a 94:6 mixture with the corresponding acetylenic alcohol: Masuyama, Y.; Watabe, A.; Ito, A.; Kurusu, Y. Chem. Commun. 2000, 2009-2010.
45. Compound (-) -9 has been isolated from the fermentation broth of ascomycete strain A23-98: Weidler, M.; Rether, J.; Anke, T.; Erkel, G.; Sterner, O. J. Antibiot. 2001, 54, 679-681.