[2 + 2] Photocycloaddition/thermal retrocycloaddition. A new entry into functionalized 5-8-5 ring systems

Journal of the American Chemical Society

Volumn 121, Issue 18, 1999, Pages 4534-4535

  Randall, Michele L ^a   Lo, Priscilla C K ^a   Bonitatebus Jr , Peter J ^a   Snapper, Marc L ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; CYCLOPENTENE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONFORMATION; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033549115     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990543c     Document Type: Article

References (51)

1. For recent advances in the construction of cyclooctanoid-containing ring systems, see: (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (b) Paquette, L. A.; Sun, L.-Q.; Watson, T. J. N.; Friedrich, D.; Freeman, B. T. J. Org. Chem. 1997, 62, 8155-8161. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Paquette, L. A.; Sturino, C. F.; Wang, X.; Prodger, J. C.; Koh, D. J. Am. Chem. Soc. 1996, 118, 5620-5633. (e) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (f) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615-3626. (g) Rigby, J. H.; McGuire, T., Senanayake, C.; Khemani, K. J. Chem. Soc. Perkin Trans. 1 1994, 3449- 3457. (h) Paquette, L. A.; Liang, S.; Wang, H.-L. J. Org. Chem. 1996, 61, 3268-3279. (i) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241-1242. (j) Wang, Y.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 876-877. (k) Dauben, W. G.; Warshawsky, A. M. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. (l) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716.
2. For recent advances in the construction of cyclooctanoid-containing ring systems, see: (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (b) Paquette, L. A.; Sun, L.-Q.; Watson, T. J. N.; Friedrich, D.; Freeman, B. T. J. Org. Chem. 1997, 62, 8155-8161. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Paquette, L. A.; Sturino, C. F.; Wang, X.; Prodger, J. C.; Koh, D. J. Am. Chem. Soc. 1996, 118, 5620-5633. (e) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (f) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615-3626. (g) Rigby, J. H.; McGuire, T., Senanayake, C.; Khemani, K. J. Chem. Soc. Perkin Trans. 1 1994, 3449- 3457. (h) Paquette, L. A.; Liang, S.; Wang, H.-L. J. Org. Chem. 1996, 61, 3268-3279. (i) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241-1242. (j) Wang, Y.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 876-877. (k) Dauben, W. G.; Warshawsky, A. M. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. (l) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716.
3. For recent advances in the construction of cyclooctanoid-containing ring systems, see: (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (b) Paquette, L. A.; Sun, L.-Q.; Watson, T. J. N.; Friedrich, D.; Freeman, B. T. J. Org. Chem. 1997, 62, 8155-8161. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Paquette, L. A.; Sturino, C. F.; Wang, X.; Prodger, J. C.; Koh, D. J. Am. Chem. Soc. 1996, 118, 5620-5633. (e) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (f) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615-3626. (g) Rigby, J. H.; McGuire, T., Senanayake, C.; Khemani, K. J. Chem. Soc. Perkin Trans. 1 1994, 3449- 3457. (h) Paquette, L. A.; Liang, S.; Wang, H.-L. J. Org. Chem. 1996, 61, 3268-3279. (i) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241-1242. (j) Wang, Y.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 876-877. (k) Dauben, W. G.; Warshawsky, A. M. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. (l) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716.
4. For recent advances in the construction of cyclooctanoid-containing ring systems, see: (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (b) Paquette, L. A.; Sun, L.-Q.; Watson, T. J. N.; Friedrich, D.; Freeman, B. T. J. Org. Chem. 1997, 62, 8155-8161. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Paquette, L. A.; Sturino, C. F.; Wang, X.; Prodger, J. C.; Koh, D. J. Am. Chem. Soc. 1996, 118, 5620-5633. (e) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (f) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615-3626. (g) Rigby, J. H.; McGuire, T., Senanayake, C.; Khemani, K. J. Chem. Soc. Perkin Trans. 1 1994, 3449- 3457. (h) Paquette, L. A.; Liang, S.; Wang, H.-L. J. Org. Chem. 1996, 61, 3268-3279. (i) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241-1242. (j) Wang, Y.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 876-877. (k) Dauben, W. G.; Warshawsky, A. M. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. (l) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716.
5. For recent advances in the construction of cyclooctanoid-containing ring systems, see: (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (b) Paquette, L. A.; Sun, L.-Q.; Watson, T. J. N.; Friedrich, D.; Freeman, B. T. J. Org. Chem. 1997, 62, 8155-8161. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Paquette, L. A.; Sturino, C. F.; Wang, X.; Prodger, J. C.; Koh, D. J. Am. Chem. Soc. 1996, 118, 5620-5633. (e) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (f) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615-3626. (g) Rigby, J. H.; McGuire, T., Senanayake, C.; Khemani, K. J. Chem. Soc. Perkin Trans. 1 1994, 3449- 3457. (h) Paquette, L. A.; Liang, S.; Wang, H.-L. J. Org. Chem. 1996, 61, 3268-3279. (i) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241-1242. (j) Wang, Y.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 876-877. (k) Dauben, W. G.; Warshawsky, A. M. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. (l) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716.
6. For recent advances in the construction of cyclooctanoid-containing ring systems, see: (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (b) Paquette, L. A.; Sun, L.-Q.; Watson, T. J. N.; Friedrich, D.; Freeman, B. T. J. Org. Chem. 1997, 62, 8155-8161. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Paquette, L. A.; Sturino, C. F.; Wang, X.; Prodger, J. C.; Koh, D. J. Am. Chem. Soc. 1996, 118, 5620-5633. (e) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (f) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615-3626. (g) Rigby, J. H.; McGuire, T., Senanayake, C.; Khemani, K. J. Chem. Soc. Perkin Trans. 1 1994, 3449- 3457. (h) Paquette, L. A.; Liang, S.; Wang, H.-L. J. Org. Chem. 1996, 61, 3268-3279. (i) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241-1242. (j) Wang, Y.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 876-877. (k) Dauben, W. G.; Warshawsky, A. M. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. (l) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716.
7. For recent advances in the construction of cyclooctanoid-containing ring systems, see: (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (b) Paquette, L. A.; Sun, L.-Q.; Watson, T. J. N.; Friedrich, D.; Freeman, B. T. J. Org. Chem. 1997, 62, 8155-8161. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Paquette, L. A.; Sturino, C. F.; Wang, X.; Prodger, J. C.; Koh, D. J. Am. Chem. Soc. 1996, 118, 5620-5633. (e) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (f) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615-3626. (g) Rigby, J. H.; McGuire, T., Senanayake, C.; Khemani, K. J. Chem. Soc. Perkin Trans. 1 1994, 3449-3457. (h) Paquette, L. A.; Liang, S.; Wang, H.-L. J. Org. Chem. 1996, 61, 3268-3279. (i) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241-1242. (j) Wang, Y.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 876-877. (k) Dauben, W. G.; Warshawsky, A. M. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. (l) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716.
8. For recent advances in the construction of cyclooctanoid-containing ring systems, see: (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (b) Paquette, L. A.; Sun, L.-Q.; Watson, T. J. N.; Friedrich, D.; Freeman, B. T. J. Org. Chem. 1997, 62, 8155-8161. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Paquette, L. A.; Sturino, C. F.; Wang, X.; Prodger, J. C.; Koh, D. J. Am. Chem. Soc. 1996, 118, 5620-5633. (e) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (f) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615-3626. (g) Rigby, J. H.; McGuire, T., Senanayake, C.; Khemani, K. J. Chem. Soc. Perkin Trans. 1 1994, 3449- 3457. (h) Paquette, L. A.; Liang, S.; Wang, H.-L. J. Org. Chem. 1996, 61, 3268-3279. (i) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241-1242. (j) Wang, Y.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 876-877. (k) Dauben, W. G.; Warshawsky, A. M. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. (l) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716.
9. For recent advances in the construction of cyclooctanoid-containing ring systems, see: (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (b) Paquette, L. A.; Sun, L.-Q.; Watson, T. J. N.; Friedrich, D.; Freeman, B. T. J. Org. Chem. 1997, 62, 8155-8161. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Paquette, L. A.; Sturino, C. F.; Wang, X.; Prodger, J. C.; Koh, D. J. Am. Chem. Soc. 1996, 118, 5620-5633. (e) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (f) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615-3626. (g) Rigby, J. H.; McGuire, T., Senanayake, C.; Khemani, K. J. Chem. Soc. Perkin Trans. 1 1994, 3449- 3457. (h) Paquette, L. A.; Liang, S.; Wang, H.-L. J. Org. Chem. 1996, 61, 3268-3279. (i) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241-1242. (j) Wang, Y.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 876-877. (k) Dauben, W. G.; Warshawsky, A. M. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. (l) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716.
10. For recent advances in the construction of cyclooctanoid-containing ring systems, see: (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (b) Paquette, L. A.; Sun, L.-Q.; Watson, T. J. N.; Friedrich, D.; Freeman, B. T. J. Org. Chem. 1997, 62, 8155-8161. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Paquette, L. A.; Sturino, C. F.; Wang, X.; Prodger, J. C.; Koh, D. J. Am. Chem. Soc. 1996, 118, 5620-5633. (e) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (f) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615-3626. (g) Rigby, J. H.; McGuire, T., Senanayake, C.; Khemani, K. J. Chem. Soc. Perkin Trans. 1 1994, 3449- 3457. (h) Paquette, L. A.; Liang, S.; Wang, H.-L. J. Org. Chem. 1996, 61, 3268-3279. (i) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241-1242. (j) Wang, Y.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 876-877. (k) Dauben, W. G.; Warshawsky, A. M. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. (l) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716.
11. For recent advances in the construction of cyclooctanoid-containing ring systems, see: (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (b) Paquette, L. A.; Sun, L.-Q.; Watson, T. J. N.; Friedrich, D.; Freeman, B. T. J. Org. Chem. 1997, 62, 8155-8161. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Paquette, L. A.; Sturino, C. F.; Wang, X.; Prodger, J. C.; Koh, D. J. Am. Chem. Soc. 1996, 118, 5620-5633. (e) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (f) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615-3626. (g) Rigby, J. H.; McGuire, T., Senanayake, C.; Khemani, K. J. Chem. Soc. Perkin Trans. 1 1994, 3449- 3457. (h) Paquette, L. A.; Liang, S.; Wang, H.-L. J. Org. Chem. 1996, 61, 3268-3279. (i) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241-1242. (j) Wang, Y.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 876-877. (k) Dauben, W. G.; Warshawsky, A. M. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. (l) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716.
12. For recent advances in the construction of cyclooctanoid-containing ring systems, see: (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930. (b) Paquette, L. A.; Sun, L.-Q.; Watson, T. J. N.; Friedrich, D.; Freeman, B. T. J. Org. Chem. 1997, 62, 8155-8161. (c) Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suárez-Sobrino, A.; Vågberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908-4909. (d) Paquette, L. A.; Sturino, C. F.; Wang, X.; Prodger, J. C.; Koh, D. J. Am. Chem. Soc. 1996, 118, 5620-5633. (e) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (f) Snider, B. B.; Yang, K. J. Org. Chem. 1992, 57, 3615-3626. (g) Rigby, J. H.; McGuire, T., Senanayake, C.; Khemani, K. J. Chem. Soc. Perkin Trans. 1 1994, 3449- 3457. (h) Paquette, L. A.; Liang, S.; Wang, H.-L. J. Org. Chem. 1996, 61, 3268-3279. (i) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241-1242. (j) Wang, Y.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 876-877. (k) Dauben, W. G.; Warshawsky, A. M. J. Chem. Soc., Chem. Commun. 1986, 1319-1321. (l) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716.
13. Pettit, R.; Henery, J. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, p 310.
14. Tallarico, J. A.; Randall, M. L.; Snapper, M. L. J. Am. Chem. Soc. 1996, 118, 9196-9197.
15. (b) Limanto, J.; Snapper, M. L. J. Org. Chem. 1998, 63, 6440-6441.
16. For an alternative cyclooctanoid-forming strategy employing cyclobutenes, see: Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479.
17. For other examples of cycloaddition/fragmentation strategies, see: (a) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (b) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (c) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (d) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (e) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (f) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (g) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 365-331. (h) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (i) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (j) Mehta, G.; Reddy, A. V.; Srikrishna, A J. Chem. Soc., Perkin Trans. 1 1986, 291-297.
18. For other examples of cycloaddition/fragmentation strategies, see: (a) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (b) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (c) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (d) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (e) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (f) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (g) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 365-331. (h) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (i) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (j) Mehta, G.; Reddy, A. V.; Srikrishna, A J. Chem. Soc., Perkin Trans. 1 1986, 291-297.
19. For other examples of cycloaddition/fragmentation strategies, see: (a) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (b) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (c) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (d) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (e) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (f) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (g) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 365-331. (h) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (i) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (j) Mehta, G.; Reddy, A. V.; Srikrishna, A J. Chem. Soc., Perkin Trans. 1 1986, 291-297.
20. For other examples of cycloaddition/fragmentation strategies, see: (a) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (b) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (c) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (d) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (e) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (f) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (g) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 365-331. (h) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (i) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (j) Mehta, G.; Reddy, A. V.; Srikrishna, A J. Chem. Soc., Perkin Trans. 1 1986, 291-297.
21. For other examples of cycloaddition/fragmentation strategies, see: (a) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (b) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (c) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (d) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (e) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (f) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (g) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 365-331. (h) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (i) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (j) Mehta, G.; Reddy, A. V.; Srikrishna, A J. Chem. Soc., Perkin Trans. 1 1986, 291-297.
22. For other examples of cycloaddition/fragmentation strategies, see: (a) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (b) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (c) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (d) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (e) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (f) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (g) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 365-331. (h) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (i) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (j) Mehta, G.; Reddy, A. V.; Srikrishna, A J. Chem. Soc., Perkin Trans. 1 1986, 291-297.
23. For other examples of cycloaddition/fragmentation strategies, see: (a) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (b) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (c) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (d) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (e) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (f) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (g) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 365-331. (h) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (i) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (j) Mehta, G.; Reddy, A. V.; Srikrishna, A J. Chem. Soc., Perkin Trans. 1 1986, 291-297.
24. For other examples of cycloaddition/fragmentation strategies, see: (a) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (b) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (c) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (d) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (e) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (f) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (g) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 365-331. (h) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (i) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (j) Mehta, G.; Reddy, A. V.; Srikrishna, A J. Chem. Soc., Perkin Trans. 1 1986, 291-297.
25. For other examples of cycloaddition/fragmentation strategies, see: (a) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (b) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (c) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (d) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (e) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (f) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (g) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 365-331. (h) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (i) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (j) Mehta, G.; Reddy, A. V.; Srikrishna, A J. Chem. Soc., Perkin Trans. 1 1986, 291-297.
26. For other examples of cycloaddition/fragmentation strategies, see: (a) Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365-367. (b) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. (c) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473. (d) Oppolzer, W. Acc. Chem. Res. 1982, 15, 135-141. (e) Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871-1874. (f) Lange, G. L.; Organ, M. G. J. Org. Chem. 1996, 61, 5358-5361. (g) Lange, G. L.; Lee, M. J. Org. Chem. 1987, 52, 365-331. (h) Kammermeier, S.; Herges, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419. (i) Prinzbach, H.; Weber, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2239-2257. (j) Mehta, G.; Reddy, A. V.; Srikrishna, A J. Chem. Soc., Perkin Trans. 1 1986, 291-297.
27. 2 atm over 12 h at 5-10°C. During this time, the reaction was irradiated (450-W Hanovia lamp) through a 6-mm Pyrex filter. The reaction was monitored by GC and stopped at approximately 80% conversion. The precipitated enone dimer was removed by filtration. Concentration, followed by silica gel chromatography, yielded the desired cycloadduct(s), as well as a small amount of the starting cyclobutene.
28. Bürgi, H.-B.; Dunitz, J. D. J. Am. Chem. Soc. 1987, 109, 2924-2926.
29. Refer to compounds 3 and 4 in eq 1 for numbering scheme.
30. (a) Martin, H.-D.; Eisenmann, E. Tetrahedron Lett. 1975, 661-664.
31. (b) Cobb, R. L.; Mahan, J. E.; Fahey, D. R. J. Org. Chem. 1977, 42, 2601-2610.
32. (c) Walsh, R.; Martin, H.-D.; Kunze, M.; Oftring, A.; Beckhaus, H.-D. J. Chem. Soc., Perkin Trans. 2 1981, 1076-1083.
33. (d) Martin, H.-D.; Hekman, M.; Rist, G.; Sauter, H.; Bellus, D. Angew. Chem., Int. Ed. Engl. 1977, 16, 406-407.
34. (e) Martin, H.-D.; Eisenmann, E.; Kunze, M.; Bonacic-Koutecky, V. Chem. Ber. 1980, 113, 1153.
35. For examples of related compounds, see: (f) Dave, P. R.; Duddu, R.; Li, J.; Surapaneni, R.; Gilardi, R. Tetrahedron Lett. 1998, 39, 5481. (g) Bakkern, F. J. A. D.; Schröer, F.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron Lett. 1998. 39, 9531-9534.
36. For examples of related compounds, see: (f) Dave, P. R.; Duddu, R.; Li, J.; Surapaneni, R.; Gilardi, R. Tetrahedron Lett. 1998, 39, 5481. (g) Bakkern, F. J. A. D.; Schröer, F.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron Lett. 1998. 39, 9531-9534.
37. For representative examples, see: (a) Sohn, M.; Blum, J.; Halpern, J. J. Am. Chem. Soc. 1979, 101, 2694-2707. (b) Wristers, J.; Brener, L.; Pettit, R. J. Am. Chem. Soc. 1970, 92, 7499-7501. (c) Paquette, L. A. Synthesis 1975, 347-357. (d) Bishop, K. C., III Chem. Rev. 1976, 76, 461-486. (e) Paquette, L. A.; Beckley, R. S.; Farnham, W. B. J. Am. Chem. Soc. 1975, 97, 1089-1100. (f) Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 9307-9308.
38. For representative examples, see: (a) Sohn, M.; Blum, J.; Halpern, J. J. Am. Chem. Soc. 1979, 101, 2694-2707. (b) Wristers, J.; Brener, L.; Pettit, R. J. Am. Chem. Soc. 1970, 92, 7499-7501. (c) Paquette, L. A. Synthesis 1975, 347-357. (d) Bishop, K. C., III Chem. Rev. 1976, 76, 461-486. (e) Paquette, L. A.; Beckley, R. S.; Farnham, W. B. J. Am. Chem. Soc. 1975, 97, 1089-1100. (f) Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 9307-9308.
39. For representative examples, see: (a) Sohn, M.; Blum, J.; Halpern, J. J. Am. Chem. Soc. 1979, 101, 2694-2707. (b) Wristers, J.; Brener, L.; Pettit, R. J. Am. Chem. Soc. 1970, 92, 7499-7501. (c) Paquette, L. A. Synthesis 1975, 347-357. (d) Bishop, K. C., III Chem. Rev. 1976, 76, 461-486. (e) Paquette, L. A.; Beckley, R. S.; Farnham, W. B. J. Am. Chem. Soc. 1975, 97, 1089-1100. (f) Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 9307-9308.
40. For representative examples, see: (a) Sohn, M.; Blum, J.; Halpern, J. J. Am. Chem. Soc. 1979, 101, 2694-2707. (b) Wristers, J.; Brener, L.; Pettit, R. J. Am. Chem. Soc. 1970, 92, 7499-7501. (c) Paquette, L. A. Synthesis 1975, 347-357. (d) Bishop, K. C., III Chem. Rev. 1976, 76, 461-486. (e) Paquette, L. A.; Beckley, R. S.; Farnham, W. B. J. Am. Chem. Soc. 1975, 97, 1089-1100. (f) Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 9307-9308.
41. For representative examples, see: (a) Sohn, M.; Blum, J.; Halpern, J. J. Am. Chem. Soc. 1979, 101, 2694-2707. (b) Wristers, J.; Brener, L.; Pettit, R. J. Am. Chem. Soc. 1970, 92, 7499-7501. (c) Paquette, L. A. Synthesis 1975, 347-357. (d) Bishop, K. C., III Chem. Rev. 1976, 76, 461-486. (e) Paquette, L. A.; Beckley, R. S.; Farnham, W. B. J. Am. Chem. Soc. 1975, 97, 1089-1100. (f) Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 9307-9308.
42. For representative examples, see: (a) Sohn, M.; Blum, J.; Halpern, J. J. Am. Chem. Soc. 1979, 101, 2694-2707. (b) Wristers, J.; Brener, L.; Pettit, R. J. Am. Chem. Soc. 1970, 92, 7499-7501. (c) Paquette, L. A. Synthesis 1975, 347-357. (d) Bishop, K. C., III Chem. Rev. 1976, 76, 461-486. (e) Paquette, L. A.; Beckley, R. S.; Farnham, W. B. J. Am. Chem. Soc. 1975, 97, 1089-1100. (f) Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 9307-9308.
43. Typical thermolysis conditions: A degassed solution of photoadduct and BHT in benzene was heated to 200-240°C in a heavy-wall sealed tube. The reaction was monitored by GC and was usually complete after 2-4 h. The reaction was concentrated, and the cyclooctanoid-containing product was purified by silica gel chromatography.
44. (a) Wiberg, K. B.; Matturro, M.; Adams, R. J. Am. Chem. Soc. 1981, 103, 1600-1602.
45. (b) v. E. Doering, W.; Roth, W. R.; Breuckmann, R.; Figge, L.; Lennartz, H.-W.; Fessner, W.-D.; Prinzbach, H. Chem. Ber. 1988, 121, 1-9.
46. (c) Schaumann, E.; Ketcham, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 225-247.
47. (d) Berson, J. A.; Tompkins, D. C.; Jones, G., III J. Am. Chem. Soc. 1970, 92, 5799-5800.
48. (e) Allred, E. L.; Hinshaw, J. C. Tetrahedron Lett. 1972, 5. 387-390.
49. (f) Roth, W. R.; Martin, M. Tetrahedron Lett. 1967, 3865-3866.
50. (a) Berson, J. A.; Dervan, P. B. J. Am. Chem. Soc. 1972, 94, 7597-7598.
51. (b) Berson, J. A.; Dervan, P. B.; Jenkins, J. A. J. Am. Chem. Soc. 1972, 94, 7598-7599.