A novel cycloisomerization of tetraenones: 4+3 Trapping of the Nazarov oxyallyl intermediate [11]

Journal of the American Chemical Society

Volumn 121, Issue 4, 1999, Pages 876-877

  Wang, Yong ^a   Arif, Atta M ^a   West, F G ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 HALOCYCLOPENTANONE; 4 PYRONE DERIVATIVE; ALKANONE; UNCLASSIFIED DRUG;

CHEMICAL BINDING; CYCLIZATION; ISOMERISM; LETTER; REACTION ANALYSIS; STEREOISOMERISM; STRUCTURE ANALYSIS; ULTRAVIOLET IRRADIATION;

EID: 0033518564     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9837001     Document Type: Letter

References (37)

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9. For recent examples, see: (a) Harmata, M.; Elomari, S. E.; Barnes, C. L. J. Am. Chem. Soc. 1996, 118, 2860. (b) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (c) Cha, J. K.; Jin, S.-J.; Choi, J.-R.; Oh, J.; Lee, D. J. Am. Chem. Soc. 1995, 117, 10914. (d) Kim, H.; Ziani-Cherif, C.; Oh, J.; Cha, J. K. J. Org. Chem. 1995, 60, 792.
10. For recent examples, see: (a) Harmata, M.; Elomari, S. E.; Barnes, C. L. J. Am. Chem. Soc. 1996, 118, 2860. (b) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (c) Cha, J. K.; Jin, S.-J.; Choi, J.-R.; Oh, J.; Lee, D. J. Am. Chem. Soc. 1995, 117, 10914. (d) Kim, H.; Ziani-Cherif, C.; Oh, J.; Cha, J. K. J. Org. Chem. 1995, 60, 792.
11. For recent examples, see: (a) Harmata, M.; Elomari, S. E.; Barnes, C. L. J. Am. Chem. Soc. 1996, 118, 2860. (b) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (c) Cha, J. K.; Jin, S.-J.; Choi, J.-R.; Oh, J.; Lee, D. J. Am. Chem. Soc. 1995, 117, 10914. (d) Kim, H.; Ziani-Cherif, C.; Oh, J.; Cha, J. K. J. Org. Chem. 1995, 60, 792.
12. (a) Bender, J. A.; Blize, A. E.; Browder, C. C.; Giese, S.; West, F. G. J. Org. Chem. 1998, 63, 2430.
13. (b) Giese, S.; West, F. G. Tetrahedron Lett. 1998, 8393.
14. (c) Browder, C. C.; West, F. G. submitted for publication.
15. Claus, R. E.; Schreiber, S. L. Org. Synth. 1985, 64, 150.
16. (a) Ikeda, Y.; Ukai, J.; Ikeda, N.; Yamamoto, H. Tetrahedron 1987, 43, 723.
17. (b) Wang, Y.; West, F. G. Manuscript in preparation.
18. Aldehyde 3a had been prepared previously by other routes: (a) Craig, D.; Geach, N. J.; Pearson, C. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071. (b) Wulff, W. D.; Powers, T. S. J. Org. Chem. 1993, 58, 2381. (c) Smith, D. A.; Houk, K. N. Tetrahedron Lett. 1991, 32, 1549. (d) Segi, M.; Takahashi, M.; Nakajima, T.; Suga, S.; Sonoda, N. Synth. Commun. 1989, 19, 2431. (e) Oppolzer, W.; Dupuis, D. Tetrahedron Lett. 1985, 26, 5437. (f) Roush, W. R.; Hall, S. E. J. Am. Chem. Soc. 1981, 103, 5200.
19. Aldehyde 3a had been prepared previously by other routes: (a) Craig, D.; Geach, N. J.; Pearson, C. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071. (b) Wulff, W. D.; Powers, T. S. J. Org. Chem. 1993, 58, 2381. (c) Smith, D. A.; Houk, K. N. Tetrahedron Lett. 1991, 32, 1549. (d) Segi, M.; Takahashi, M.; Nakajima, T.; Suga, S.; Sonoda, N. Synth. Commun. 1989, 19, 2431. (e) Oppolzer, W.; Dupuis, D. Tetrahedron Lett. 1985, 26, 5437. (f) Roush, W. R.; Hall, S. E. J. Am. Chem. Soc. 1981, 103, 5200.
20. Aldehyde 3a had been prepared previously by other routes: (a) Craig, D.; Geach, N. J.; Pearson, C. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071. (b) Wulff, W. D.; Powers, T. S. J. Org. Chem. 1993, 58, 2381. (c) Smith, D. A.; Houk, K. N. Tetrahedron Lett. 1991, 32, 1549. (d) Segi, M.; Takahashi, M.; Nakajima, T.; Suga, S.; Sonoda, N. Synth. Commun. 1989, 19, 2431. (e) Oppolzer, W.; Dupuis, D. Tetrahedron Lett. 1985, 26, 5437. (f) Roush, W. R.; Hall, S. E. J. Am. Chem. Soc. 1981, 103, 5200.
21. Aldehyde 3a had been prepared previously by other routes: (a) Craig, D.; Geach, N. J.; Pearson, C. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071. (b) Wulff, W. D.; Powers, T. S. J. Org. Chem. 1993, 58, 2381. (c) Smith, D. A.; Houk, K. N. Tetrahedron Lett. 1991, 32, 1549. (d) Segi, M.; Takahashi, M.; Nakajima, T.; Suga, S.; Sonoda, N. Synth. Commun. 1989, 19, 2431. (e) Oppolzer, W.; Dupuis, D. Tetrahedron Lett. 1985, 26, 5437. (f) Roush, W. R.; Hall, S. E. J. Am. Chem. Soc. 1981, 103, 5200.
22. Aldehyde 3a had been prepared previously by other routes: (a) Craig, D.; Geach, N. J.; Pearson, C. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071. (b) Wulff, W. D.; Powers, T. S. J. Org. Chem. 1993, 58, 2381. (c) Smith, D. A.; Houk, K. N. Tetrahedron Lett. 1991, 32, 1549. (d) Segi, M.; Takahashi, M.; Nakajima, T.; Suga, S.; Sonoda, N. Synth. Commun. 1989, 19, 2431. (e) Oppolzer, W.; Dupuis, D. Tetrahedron Lett. 1985, 26, 5437. (f) Roush, W. R.; Hall, S. E. J. Am. Chem. Soc. 1981, 103, 5200.
23. Aldehyde 3a had been prepared previously by other routes: (a) Craig, D.; Geach, N. J.; Pearson, C. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071. (b) Wulff, W. D.; Powers, T. S. J. Org. Chem. 1993, 58, 2381. (c) Smith, D. A.; Houk, K. N. Tetrahedron Lett. 1991, 32, 1549. (d) Segi, M.; Takahashi, M.; Nakajima, T.; Suga, S.; Sonoda, N. Synth. Commun. 1989, 19, 2431. (e) Oppolzer, W.; Dupuis, D. Tetrahedron Lett. 1985, 26, 5437. (f) Roush, W. R.; Hall, S. E. J. Am. Chem. Soc. 1981, 103, 5200.
24. 3 in silicon-directed Nazarov reactions, see: Denmark, S. E.; Jones, T. K. J. Am. Chem. Soc. 1982, 104, 2642. Other Lewis acids: (b) Tsuge, O.; Kanemasa, S.; Fujiwara, I.; Wada, E. Bull. Chem. Soc. Jpn. 1987, 60, 325. (c) Santelli, M.; Dulcere, J.-P.; Morel-Fourrier, C. J. Am. Chem. Soc. 1991, 113, 8062. (d) Marino, J. P.; Linderman, R. J. J. Org. Chem. 1981, 46, 3696.
25. 3 in silicon-directed Nazarov reactions, see: Denmark, S. E.; Jones, T. K. J. Am. Chem. Soc. 1982, 104, 2642. Other Lewis acids: (b) Tsuge, O.; Kanemasa, S.; Fujiwara, I.; Wada, E. Bull. Chem. Soc. Jpn. 1987, 60, 325. (c) Santelli, M.; Dulcere, J.-P.; Morel-Fourrier, C. J. Am. Chem. Soc. 1991, 113, 8062. (d) Marino, J. P.; Linderman, R. J. J. Org. Chem. 1981, 46, 3696.
26. 3 in silicon-directed Nazarov reactions, see: Denmark, S. E.; Jones, T. K. J. Am. Chem. Soc. 1982, 104, 2642. Other Lewis acids: (b) Tsuge, O.; Kanemasa, S.; Fujiwara, I.; Wada, E. Bull. Chem. Soc. Jpn. 1987, 60, 325. (c) Santelli, M.; Dulcere, J.-P.; Morel-Fourrier, C. J. Am. Chem. Soc. 1991, 113, 8062. (d) Marino, J. P.; Linderman, R. J. J. Org. Chem. 1981, 46, 3696.
27. 3 in silicon-directed Nazarov reactions, see: Denmark, S. E.; Jones, T. K. J. Am. Chem. Soc. 1982, 104, 2642. Other Lewis acids: (b) Tsuge, O.; Kanemasa, S.; Fujiwara, I.; Wada, E. Bull. Chem. Soc. Jpn. 1987, 60, 325. (c) Santelli, M.; Dulcere, J.-P.; Morel-Fourrier, C. J. Am. Chem. Soc. 1991, 113, 8062. (d) Marino, J. P.; Linderman, R. J. J. Org. Chem. 1981, 46, 3696.
28. 5b
29. (a) The stereochemistry of 7a and 8a was assigned based on close spectral analogy to 7b and 8b. (b) The stereochemistry of 8d was rigorously determined by X-ray diffraction analysis, and that of 8c was assigned based on close spectral analogy to 8d.
30. Endo and exo refer to the orientation of the diene in relation to the central carbon of the oxyallyl unit. There is some precedent for greater exo/ endo selectivity in intramolecular [4+3]- and [4+4]-cycloadditions: (a) Harmata, M.; Herron, B. F. J. Org. Chem. 1993, 58, 7393. (b) Sieburth, S. McN.; Hiel, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (c) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J. J. Am. Chem. Soc. 1996, 118, 10803.
31. Endo and exo refer to the orientation of the diene in relation to the central carbon of the oxyallyl unit. There is some precedent for greater exo/ endo selectivity in intramolecular [4+3]- and [4+4]-cycloadditions: (a) Harmata, M.; Herron, B. F. J. Org. Chem. 1993, 58, 7393. (b) Sieburth, S. McN.; Hiel, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (c) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J. J. Am. Chem. Soc. 1996, 118, 10803.
32. Endo and exo refer to the orientation of the diene in relation to the central carbon of the oxyallyl unit. There is some precedent for greater exo/ endo selectivity in intramolecular [4+3]- and [4+4]-cycloadditions: (a) Harmata, M.; Herron, B. F. J. Org. Chem. 1993, 58, 7393. (b) Sieburth, S. McN.; Hiel, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (c) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J. J. Am. Chem. Soc. 1996, 118, 10803.
33. 5c
34. 5c
35. Takano, S.; Inomata, K.; Samizu, K.; Tomita, S.; Yanase, M.; Suzuki, M.; Iwabuchi, Y.; Sugihara, T.; Ogasawara, K. Chem. Lett. 1989, 1283. The reaction was not complete after stirring for 3 days following the literature procedure; however, we have found that the reaction went to completion in 12 h in the presence of silica gel.
36. (a) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
37. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.