The tandem Pummerer-isomunchnone route to (±)-pumiliotoxin C

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1505-1508

  Kuethe, Jeffrey T ^a   Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; PUMILIOTOXIN;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; HYDROGENATION; REACTION ANALYSIS;

EID: 0031550812     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00141-X     Document Type: Article

References (32)

1. 1. Witkop, B.; Gossinger, E. In Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1983; Vol 21, p 190.
2. 2. Daly, J. W.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley-Interscience: New York, 1986; Vol 4, pp 1-274.
3. 3. Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H. P. Tetrahedron Lett. 1986, 27, 1569. Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493. Toyota, M.; Takanobu, A.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697. Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103. Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652. Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279.
4. 3. Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H. P. Tetrahedron Lett. 1986, 27, 1569. Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493. Toyota, M.; Takanobu, A.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697. Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103. Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652. Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279.
5. 3. Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H. P. Tetrahedron Lett. 1986, 27, 1569. Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493. Toyota, M.; Takanobu, A.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697. Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103. Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652. Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279.
6. 3. Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H. P. Tetrahedron Lett. 1986, 27, 1569. Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493. Toyota, M.; Takanobu, A.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697. Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103. Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652. Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279.
7. 3. Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H. P. Tetrahedron Lett. 1986, 27, 1569. Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493. Toyota, M.; Takanobu, A.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697. Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103. Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652. Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279.
8. 3. Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H. P. Tetrahedron Lett. 1986, 27, 1569. Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493. Toyota, M.; Takanobu, A.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697. Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103. Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652. Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279.
9. 3. Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H. P. Tetrahedron Lett. 1986, 27, 1569. Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493. Toyota, M.; Takanobu, A.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697. Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103. Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652. Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279.
10. 3. Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H. P. Tetrahedron Lett. 1986, 27, 1569. Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493. Toyota, M.; Takanobu, A.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697. Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103. Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652. Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279.
11. 3. Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H. P. Tetrahedron Lett. 1986, 27, 1569. Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493. Toyota, M.; Takanobu, A.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697. Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103. Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652. Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279.
12. 3. Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H. P. Tetrahedron Lett. 1986, 27, 1569. Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493. Toyota, M.; Takanobu, A.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697. Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103. Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652. Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279.
13. 3. Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H. P. Tetrahedron Lett. 1986, 27, 1569. Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493. Toyota, M.; Takanobu, A.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697. Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103. Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652. Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279.
14. 3. Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H. P. Tetrahedron Lett. 1986, 27, 1569. Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493. Toyota, M.; Takanobu, A.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697. Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103. Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652. Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279.
15. 4. Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123.
16. 5. Marino, J. P., Jr.; Osterhout, M. H.; Padwa, A. J. Org. Chem. 1995, 60, 2704.
17. 6. DeLucchi, O.; Miotti, U.; Modena, G. Organic Reactions; Paquette, L. A., Ed.; John Wiley: New York, 1991, Chap. 3, pp 157-184. Grierson, D. S.; Husson, H. P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991, Vol 6, pp 909-947.
18. 6. DeLucchi, O.; Miotti, U.; Modena, G. Organic Reactions; Paquette, L. A., Ed.; John Wiley: New York, 1991, Chap. 3, pp 157-184. Grierson, D. S.; Husson, H. P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991, Vol 6, pp 909-947.
19. 7. Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 3495. Cochran, J. E.; Padwa, A., J. Org. Chem. 1995, 60, 3938. Padwa, A.; Cochran, J. E.; Kappe, C. O. J. Org. Chem. 1996, 61, 3706. Padwa, A.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1996, 61, 4888. Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166.
20. 7. Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 3495. Cochran, J. E.; Padwa, A., J. Org. Chem. 1995, 60, 3938. Padwa, A.; Cochran, J. E.; Kappe, C. O. J. Org. Chem. 1996, 61, 3706. Padwa, A.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1996, 61, 4888. Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166.
21. 7. Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 3495. Cochran, J. E.; Padwa, A., J. Org. Chem. 1995, 60, 3938. Padwa, A.; Cochran, J. E.; Kappe, C. O. J. Org. Chem. 1996, 61, 3706. Padwa, A.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1996, 61, 4888. Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166.
22. 7. Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 3495. Cochran, J. E.; Padwa, A., J. Org. Chem. 1995, 60, 3938. Padwa, A.; Cochran, J. E.; Kappe, C. O. J. Org. Chem. 1996, 61, 3706. Padwa, A.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1996, 61, 4888. Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166.
23. 7. Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 3495. Cochran, J. E.; Padwa, A., J. Org. Chem. 1995, 60, 3938. Padwa, A.; Cochran, J. E.; Kappe, C. O. J. Org. Chem. 1996, 61, 3706. Padwa, A.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1996, 61, 4888. Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166.
24. 8. Padwa, A.; Kuethe, J. T. J. Org. Chem. 1997, 62, in press.
25. 9. Imidosulfoxide 5 was prepared in 3 steps from 6-heptenoic acid by conversion to the corresponding N-benzylamide followed by reaction with ethylsulfenylacetyl chloride and oxidation using sodium periodate.
26. 10. McMurray, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
27. 11. Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1984, 25, 4821.
28. 12. Ibuka, T.; Masaki, N.; Saji, I.; Tanaka, K.; Inubushi, Y. Chem. Pharm. Bull. 1975, 23, 2779.
29. 13. Mabic, S.; Castagnoli, N., Jr. J. Org. Chem. 1996, 61, 309.
30. 14. Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. Tetrahedron 1993, 49, 8805.
31. 15. Oppolzer, W.; Fehr, C.; Warneke, J. Helv. Chim. Acta 1977, 60, 48. Maruola, K.; Miyazaki, T.; Ando, M.; Matsumura, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831.
32. 15. Oppolzer, W.; Fehr, C.; Warneke, J. Helv. Chim. Acta 1977, 60, 48. Maruola, K.; Miyazaki, T.; Ando, M.; Matsumura, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831.