Construction of the azepinoindole core tricycle of the Stemona alkaloids

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5587-5591

  Rigby, James H ^a   Laurent, Stéphane ^a   Cavezza, Alexandre ^a   Heeg, Mary Jane ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; AZEPINOINDOLE; AZEPINOINDOLE DERIVATIVE; INDOLE DERIVATIVE; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; BRONCHITIS; CYCLIZATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; PERTUSSIS; RESPIRATORY TRACT DISEASE; TUBERCULOSIS;

EID: 0031880140     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980916c     Document Type: Article

References (43)

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5. For total syntheses of stenine, see: (a) Chen, C.-y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236. (b) Chen, C.-y.; Hart, D. J. Ibid. 1993, 58, 3840. Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106. Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904.
6. For total syntheses of stenine, see: (a) Chen, C.-y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236. (b) Chen, C.-y.; Hart, D. J. Ibid. 1993, 58, 3840. Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106. Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904.
7. For total syntheses of stenine, see: (a) Chen, C.-y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236. (b) Chen, C.-y.; Hart, D. J. Ibid. 1993, 58, 3840. Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106. Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904.
8. For total syntheses of stenine, see: (a) Chen, C.-y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236. (b) Chen, C.-y.; Hart, D. J. Ibid. 1993, 58, 3840. Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106. Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904.
9. For additional approaches into the azepinoindole system, see: (a) Xiang, L.; Kozikowski, A. P. Synlett 1990, 279. (b) Wipf, P.; Kim, V. Tetrahedron Lett. 1992, 33, 5477.
10. For additional approaches into the azepinoindole system, see: (a) Xiang, L.; Kozikowski, A. P. Synlett 1990, 279. (b) Wipf, P.; Kim, V. Tetrahedron Lett. 1992, 33, 5477.
11. Goldstein, D. M.; Wipf, P. Ibid. 1996, 37, 739.
12. For approaches to other Stemona alkaloids not possessing the azepinoindole substructure, see: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Beddoes, R. L.; Davies, M. P. H.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1992, 538. Martin, S. F.; Corbett, J. W. Synthesis 1992, 55. Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773. (e) Williams, D. R.; Reddy, J. P.; Amato, G. S. Ibid. 1994, 35, 6417. (f) Morimoto, Y.; Iwahashi, M. Synlett 1995, 1221.
13. For approaches to other Stemona alkaloids not possessing the azepinoindole substructure, see: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Beddoes, R. L.; Davies, M. P. H.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1992, 538. Martin, S. F.; Corbett, J. W. Synthesis 1992, 55. Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773. (e) Williams, D. R.; Reddy, J. P.; Amato, G. S. Ibid. 1994, 35, 6417. (f) Morimoto, Y.; Iwahashi, M. Synlett 1995, 1221.
14. For approaches to other Stemona alkaloids not possessing the azepinoindole substructure, see: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Beddoes, R. L.; Davies, M. P. H.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1992, 538. Martin, S. F.; Corbett, J. W. Synthesis 1992, 55. Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773. (e) Williams, D. R.; Reddy, J. P.; Amato, G. S. Ibid. 1994, 35, 6417. (f) Morimoto, Y.; Iwahashi, M. Synlett 1995, 1221.
15. For approaches to other Stemona alkaloids not possessing the azepinoindole substructure, see: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Beddoes, R. L.; Davies, M. P. H.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1992, 538. Martin, S. F.; Corbett, J. W. Synthesis 1992, 55. Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773. (e) Williams, D. R.; Reddy, J. P.; Amato, G. S. Ibid. 1994, 35, 6417. (f) Morimoto, Y.; Iwahashi, M. Synlett 1995, 1221.
16. For approaches to other Stemona alkaloids not possessing the azepinoindole substructure, see: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Beddoes, R. L.; Davies, M. P. H.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1992, 538. Martin, S. F.; Corbett, J. W. Synthesis 1992, 55. Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773. (e) Williams, D. R.; Reddy, J. P.; Amato, G. S. Ibid. 1994, 35, 6417. (f) Morimoto, Y.; Iwahashi, M. Synlett 1995, 1221.
17. For approaches to other Stemona alkaloids not possessing the azepinoindole substructure, see: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Beddoes, R. L.; Davies, M. P. H.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1992, 538. Martin, S. F.; Corbett, J. W. Synthesis 1992, 55. Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773. (e) Williams, D. R.; Reddy, J. P.; Amato, G. S. Ibid. 1994, 35, 6417. (f) Morimoto, Y.; Iwahashi, M. Synlett 1995, 1221.
18. Rigby, J. H.; Cavezza, A.; Ahmed, G. J. Am. Chem. Soc. 1996, 118, 12848.
19. Rigby, J. H.; Qabar, M.; Ahmed, G.; Hughes, R. C. Tetrahedron 1993, 49, 10219.
20. For recent examples of 7-endo radical cyclizations, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Synlett 1997, 1391. Lee, E.; Lim, J. W.; Yoon, C. H.; Sung, Y.-s.; Kim, Y. K.; Yun, M.; Kim, S. J. Am. Chem. Soc. 1997, 119, 8391. Gibson, S. E.; Guillo, N.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 1997, 637. (e) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659. (g) Moody, C. J.; Norton, C. L. Ibid. 1995, 36, 9051. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943. Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031. (j) Ghosh, A. K.; Ghosh, K.; Pal, S.; Chatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809. (k) Fidalgo, J.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1993, 34, 7317. Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175. Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (n) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
21. For recent examples of 7-endo radical cyclizations, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Synlett 1997, 1391. Lee, E.; Lim, J. W.; Yoon, C. H.; Sung, Y.-s.; Kim, Y. K.; Yun, M.; Kim, S. J. Am. Chem. Soc. 1997, 119, 8391. Gibson, S. E.; Guillo, N.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 1997, 637. (e) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659. (g) Moody, C. J.; Norton, C. L. Ibid. 1995, 36, 9051. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943. Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031. (j) Ghosh, A. K.; Ghosh, K.; Pal, S.; Chatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809. (k) Fidalgo, J.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1993, 34, 7317. Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175. Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (n) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
22. For recent examples of 7-endo radical cyclizations, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Synlett 1997, 1391. Lee, E.; Lim, J. W.; Yoon, C. H.; Sung, Y.-s.; Kim, Y. K.; Yun, M.; Kim, S. J. Am. Chem. Soc. 1997, 119, 8391. Gibson, S. E.; Guillo, N.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 1997, 637. (e) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659. (g) Moody, C. J.; Norton, C. L. Ibid. 1995, 36, 9051. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943. Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031. (j) Ghosh, A. K.; Ghosh, K.; Pal, S.; Chatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809. (k) Fidalgo, J.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1993, 34, 7317. Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175. Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (n) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
23. For recent examples of 7-endo radical cyclizations, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Synlett 1997, 1391. Lee, E.; Lim, J. W.; Yoon, C. H.; Sung, Y.-s.; Kim, Y. K.; Yun, M.; Kim, S. J. Am. Chem. Soc. 1997, 119, 8391. Gibson, S. E.; Guillo, N.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 1997, 637. (e) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659. (g) Moody, C. J.; Norton, C. L. Ibid. 1995, 36, 9051. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943. Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031. (j) Ghosh, A. K.; Ghosh, K.; Pal, S.; Chatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809. (k) Fidalgo, J.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1993, 34, 7317. Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175. Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (n) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
24. For recent examples of 7-endo radical cyclizations, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Synlett 1997, 1391. Lee, E.; Lim, J. W.; Yoon, C. H.; Sung, Y.-s.; Kim, Y. K.; Yun, M.; Kim, S. J. Am. Chem. Soc. 1997, 119, 8391. Gibson, S. E.; Guillo, N.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 1997, 637. (e) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659. (g) Moody, C. J.; Norton, C. L. Ibid. 1995, 36, 9051. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943. Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031. (j) Ghosh, A. K.; Ghosh, K.; Pal, S.; Chatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809. (k) Fidalgo, J.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1993, 34, 7317. Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175. Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (n) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
25. For recent examples of 7-endo radical cyclizations, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Synlett 1997, 1391. Lee, E.; Lim, J. W.; Yoon, C. H.; Sung, Y.-s.; Kim, Y. K.; Yun, M.; Kim, S. J. Am. Chem. Soc. 1997, 119, 8391. Gibson, S. E.; Guillo, N.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 1997, 637. (e) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659. (g) Moody, C. J.; Norton, C. L. Ibid. 1995, 36, 9051. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943. Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031. (j) Ghosh, A. K.; Ghosh, K.; Pal, S.; Chatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809. (k) Fidalgo, J.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1993, 34, 7317. Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175. Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (n) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
26. For recent examples of 7-endo radical cyclizations, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Synlett 1997, 1391. Lee, E.; Lim, J. W.; Yoon, C. H.; Sung, Y.-s.; Kim, Y. K.; Yun, M.; Kim, S. J. Am. Chem. Soc. 1997, 119, 8391. Gibson, S. E.; Guillo, N.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 1997, 637. (e) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659. (g) Moody, C. J.; Norton, C. L. Ibid. 1995, 36, 9051. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943. Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031. (j) Ghosh, A. K.; Ghosh, K.; Pal, S.; Chatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809. (k) Fidalgo, J.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1993, 34, 7317. Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175. Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (n) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
27. For recent examples of 7-endo radical cyclizations, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Synlett 1997, 1391. Lee, E.; Lim, J. W.; Yoon, C. H.; Sung, Y.-s.; Kim, Y. K.; Yun, M.; Kim, S. J. Am. Chem. Soc. 1997, 119, 8391. Gibson, S. E.; Guillo, N.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 1997, 637. (e) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659. (g) Moody, C. J.; Norton, C. L. Ibid. 1995, 36, 9051. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943. Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031. (j) Ghosh, A. K.; Ghosh, K.; Pal, S.; Chatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809. (k) Fidalgo, J.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1993, 34, 7317. Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175. Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (n) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
28. For recent examples of 7-endo radical cyclizations, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Synlett 1997, 1391. Lee, E.; Lim, J. W.; Yoon, C. H.; Sung, Y.-s.; Kim, Y. K.; Yun, M.; Kim, S. J. Am. Chem. Soc. 1997, 119, 8391. Gibson, S. E.; Guillo, N.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 1997, 637. (e) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659. (g) Moody, C. J.; Norton, C. L. Ibid. 1995, 36, 9051. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943. Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031. (j) Ghosh, A. K.; Ghosh, K.; Pal, S.; Chatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809. (k) Fidalgo, J.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1993, 34, 7317. Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175. Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (n) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
29. For recent examples of 7-endo radical cyclizations, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Synlett 1997, 1391. Lee, E.; Lim, J. W.; Yoon, C. H.; Sung, Y.-s.; Kim, Y. K.; Yun, M.; Kim, S. J. Am. Chem. Soc. 1997, 119, 8391. Gibson, S. E.; Guillo, N.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 1997, 637. (e) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659. (g) Moody, C. J.; Norton, C. L. Ibid. 1995, 36, 9051. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943. Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031. (j) Ghosh, A. K.; Ghosh, K.; Pal, S.; Chatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809. (k) Fidalgo, J.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1993, 34, 7317. Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175. Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (n) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
30. For recent examples of 7-endo radical cyclizations, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Synlett 1997, 1391. Lee, E.; Lim, J. W.; Yoon, C. H.; Sung, Y.-s.; Kim, Y. K.; Yun, M.; Kim, S. J. Am. Chem. Soc. 1997, 119, 8391. Gibson, S. E.; Guillo, N.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 1997, 637. (e) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659. (g) Moody, C. J.; Norton, C. L. Ibid. 1995, 36, 9051. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943. Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031. (j) Ghosh, A. K.; Ghosh, K.; Pal, S.; Chatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809. (k) Fidalgo, J.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1993, 34, 7317. Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175. Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (n) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
31. For recent examples of 7-endo radical cyclizations, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Synlett 1997, 1391. Lee, E.; Lim, J. W.; Yoon, C. H.; Sung, Y.-s.; Kim, Y. K.; Yun, M.; Kim, S. J. Am. Chem. Soc. 1997, 119, 8391. Gibson, S. E.; Guillo, N.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 1997, 637. (e) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659. (g) Moody, C. J.; Norton, C. L. Ibid. 1995, 36, 9051. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943. Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031. (j) Ghosh, A. K.; Ghosh, K.; Pal, S.; Chatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809. (k) Fidalgo, J.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1993, 34, 7317. Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175. Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (n) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
32. For recent examples of 7-endo radical cyclizations, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Synlett 1997, 1391. Lee, E.; Lim, J. W.; Yoon, C. H.; Sung, Y.-s.; Kim, Y. K.; Yun, M.; Kim, S. J. Am. Chem. Soc. 1997, 119, 8391. Gibson, S. E.; Guillo, N.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 1997, 637. (e) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659. (g) Moody, C. J.; Norton, C. L. Ibid. 1995, 36, 9051. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943. Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031. (j) Ghosh, A. K.; Ghosh, K.; Pal, S.; Chatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809. (k) Fidalgo, J.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1993, 34, 7317. Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175. Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (n) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
33. For recent examples of 7-endo radical cyclizations, see: (a) Ripa, L.; Hallberg, A. J. Org. Chem. 1998, 63, 84. (b) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Synlett 1997, 1391. Lee, E.; Lim, J. W.; Yoon, C. H.; Sung, Y.-s.; Kim, Y. K.; Yun, M.; Kim, S. J. Am. Chem. Soc. 1997, 119, 8391. Gibson, S. E.; Guillo, N.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 1997, 637. (e) Rodríguez, G.; Cid, M. M.; Saá, C.; Castedo, L.; Domínguez, D. J. Org. Chem. 1996, 61, 2780. (f) Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659. (g) Moody, C. J.; Norton, C. L. Ibid. 1995, 36, 9051. (h) Brown, C. D. S.; Dishington, A. P.; Shishkin, O.; Simpkins, N. S. Synlett 1995, 943. Colombo, L.; Di Giacomo, M.; Papeo, G.; Carugo, O.; Scolastico, C.; Manzoni, L. Tetrahedron Lett. 1994, 35, 4031. (j) Ghosh, A. K.; Ghosh, K.; Pal, S.; Chatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809. (k) Fidalgo, J.; Castedo, L.; Domínguez, D. Tetrahedron Lett. 1993, 34, 7317. Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175. Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (n) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
34. Rigby, J. H.; Qabar, M. N. J. Org. Chem. 1993, 58, 4473.
35. Calculations (SYBYL force field) performed on Spartan SGI (copyright 1991-95, Wave Function, Inc.) suggest that the all-cis ring fusion stereochemistry is more stable than the cis-trans isomer by at least 1 kcal/mol. We thank Sylvie Bosio of this department for performing these calculations.
36. 13C NMR, IR) and analytical (combustion analysis and/or HRMS) data in complete accord with the assigned structure.
37. X-ray data for this compound have been deposited with the Cambridge Crystallographic Data Centre.
38. Rigby, J. H.; Qabar, M. J. Am. Chem. Soc. 1991, 113, 8975.
39. Stork, G.; Dowd, S. R. J. Am. Chem. Soc. 1963, 55, 2178.
40. Rigby, J. H.; Mateo, M. E. Tetrahedron 1996, 52, 10569.
41. max (nm) = 256, 430) characteristic of the chromophore present in the assigned structure.
42. Qabar, M. Ph.D. Thesis, Wayne State University, 1991.
43. General experimental details have been described previously: Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S, V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am Chem. Soc. 1993, 115, 1382.