Intramolecular hetero Diels-Alder (Povarov) approach to the synthesis of the alkaloids luotonin A and camptothecin

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4913-4916

  Twin, Heather ^a   Batey, Robert A ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKALOID; CAMPTOTHECIN; IMINE; LEWIS ACID;

ARTICLE; CATALYSIS; CATALYST; DIELS ALDER REACTION; MOLECULE; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 12344256758     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0479848     Document Type: Article

References (49)

1. For a review on the hetero Diels-Alder reaction see: Buonora, P.; Olsen, J.-C.; Oh, T. Tetrahedron 2001, 57, 6099-6138.
2. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656-670 and references therein.
3. For a review of tetrahydroquinoline synthesis, see: Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031-15070.
4. For recent reviews on multicomponent reactions, see: (a) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471-1499. (b) Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144. (c) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (d) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321-3329.
5. For recent reviews on multicomponent reactions, see: (a) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471-1499. (b) Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144. (c) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (d) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321-3329.
6. For recent reviews on multicomponent reactions, see: (a) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471-1499. (b) Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144. (c) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (d) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321-3329.
7. For recent reviews on multicomponent reactions, see: (a) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471-1499. (b) Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144. (c) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210. (d) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321-3329.
8. Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913-2916.
9. Xia, C. F.; Heng, L. S.; Ma, D. W. Tetrahedron Lett. 2002, 43, 9405-9409.
10. Osborne, D.; Stevenson, P. J. Tetrahedron Lett. 2002, 43, 5469-5470.
11. Wall, M. E.; Wani, M. C.; Cook, C. E.; Palmer, K. H.; MacPhail, A. T.; Sim, G. A. J. Am. Chem. Soc. 1966, 88, 3888-3890.
12. For a recent review on Camptothecins, see: Du, W. Tetrahedron 2003, 59, 8649-8687.
13. 2 C-C bond formation followed by N-alkylation, see: (a) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (b) Comins, D. L.; Nolan, J. M. Org. Lett. 2001, 3, 4255-4257. (c) Bennasar, M.-L.; Zulaica, E.; Juan, C.; Alonso, Y.; Bosch, J. J. Org. Chem. 2002, 67, 7465-7474.
14. 2 C-C bond formation followed by N-alkylation, see: (a) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (b) Comins, D. L.; Nolan, J. M. Org. Lett. 2001, 3, 4255-4257. (c) Bennasar, M.-L.; Zulaica, E.; Juan, C.; Alonso, Y.; Bosch, J. J. Org. Chem. 2002, 67, 7465-7474.
15. 2 C-C bond formation followed by N-alkylation, see: (a) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (b) Comins, D. L.; Nolan, J. M. Org. Lett. 2001, 3, 4255-4257. (c) Bennasar, M.-L.; Zulaica, E.; Juan, C.; Alonso, Y.; Bosch, J. J. Org. Chem. 2002, 67, 7465-7474.
16. For approaches involving construction of the B and C rings using a 4 + 1 radical annulation reaction, see: (a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (b) Curran, D. P.; Liu, H.; Josien, H.; Ko, S.-B. Tetrahedron 1996, 52, 11385-11404. (c) Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215-3218. (d) Bowman, W. R.; Bridge, C. F.; Brookes, P.; Cloonan, M. O.; Leach, D. C. J. Chem. Soc., Perkin Trans. 1 2002, 58-68.
17. For approaches involving construction of the B and C rings using a 4 + 1 radical annulation reaction, see: (a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (b) Curran, D. P.; Liu, H.; Josien, H.; Ko, S.-B. Tetrahedron 1996, 52, 11385-11404. (c) Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215-3218. (d) Bowman, W. R.; Bridge, C. F.; Brookes, P.; Cloonan, M. O.; Leach, D. C. J. Chem. Soc., Perkin Trans. 1 2002, 58-68.
18. For approaches involving construction of the B and C rings using a 4 + 1 radical annulation reaction, see: (a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (b) Curran, D. P.; Liu, H.; Josien, H.; Ko, S.-B. Tetrahedron 1996, 52, 11385-11404. (c) Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215-3218. (d) Bowman, W. R.; Bridge, C. F.; Brookes, P.; Cloonan, M. O.; Leach, D. C. J. Chem. Soc., Perkin Trans. 1 2002, 58-68.
19. For approaches involving construction of the B and C rings using a 4 + 1 radical annulation reaction, see: (a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (b) Curran, D. P.; Liu, H.; Josien, H.; Ko, S.-B. Tetrahedron 1996, 52, 11385-11404. (c) Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215-3218. (d) Bowman, W. R.; Bridge, C. F.; Brookes, P.; Cloonan, M. O.; Leach, D. C. J. Chem. Soc., Perkin Trans. 1 2002, 58-68.
20. For Friedlander condensation approaches to form the B ring, see: (a) Hutchinson, C. R. Tetrahedron 1981, 37, 1047-1065. (b) Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. Tetrahedron Lett. 1989, 30, 2639-2640. (c) Jew, S.-S.; Ok, K.-D.; Kim, H.-J.; Kim, M. G.; Kim, J. M.; Cho, Y.-S. Tetrahedron: Asymmetry 1995, 6, 1245-1248. (d) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1997, 62, 6588-6597.
21. For Friedlander condensation approaches to form the B ring, see: (a) Hutchinson, C. R. Tetrahedron 1981, 37, 1047-1065. (b) Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. Tetrahedron Lett. 1989, 30, 2639-2640. (c) Jew, S.-S.; Ok, K.-D.; Kim, H.-J.; Kim, M. G.; Kim, J. M.; Cho, Y.-S. Tetrahedron: Asymmetry 1995, 6, 1245-1248. (d) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1997, 62, 6588-6597.
22. For Friedlander condensation approaches to form the B ring, see: (a) Hutchinson, C. R. Tetrahedron 1981, 37, 1047-1065. (b) Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. Tetrahedron Lett. 1989, 30, 2639-2640. (c) Jew, S.-S.; Ok, K.-D.; Kim, H.-J.; Kim, M. G.; Kim, J. M.; Cho, Y.-S. Tetrahedron: Asymmetry 1995, 6, 1245-1248. (d) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1997, 62, 6588-6597.
23. For Friedlander condensation approaches to form the B ring, see: (a) Hutchinson, C. R. Tetrahedron 1981, 37, 1047-1065. (b) Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. Tetrahedron Lett. 1989, 30, 2639-2640. (c) Jew, S.-S.; Ok, K.-D.; Kim, H.-J.; Kim, M. G.; Kim, J. M.; Cho, Y.-S. Tetrahedron: Asymmetry 1995, 6, 1245-1248. (d) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1997, 62, 6588-6597.
24. For inter- or intramolecular Michael addition approaches to D ring construction, see: (a) Ciufolini, M. A.; Roschangar, F. Tetrahedron 1997, 53, 11049-11060. (b) Chavan, S. P.; Venkatraman, M. S. Tetrahedron Lett. 1998, 39, 6745-6748.
25. For inter- or intramolecular Michael addition approaches to D ring construction, see: (a) Ciufolini, M. A.; Roschangar, F. Tetrahedron 1997, 53, 11049-11060. (b) Chavan, S. P.; Venkatraman, M. S. Tetrahedron Lett. 1998, 39, 6745-6748.
26. For Diels-Alder reaction approaches to B, C, and D ring formation, see: (a) Fortunak, J. M. D.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5679-5682. (b) Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (c) Blagg, B. S. J.; Boger, D. L. Tetrahedron 2002, 58, 6343-6349. (d) Toyata, M.; Komori, C.; Ihara, M. J. Org. Chem. 2000, 65, 7110-7113. (e) Rigby, J. H.; Danca, D. M. Tetrahedron Lett. 1997, 38, 4969-4972.
27. For Diels-Alder reaction approaches to B, C, and D ring formation, see: (a) Fortunak, J. M. D.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5679-5682. (b) Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (c) Blagg, B. S. J.; Boger, D. L. Tetrahedron 2002, 58, 6343-6349. (d) Toyata, M.; Komori, C.; Ihara, M. J. Org. Chem. 2000, 65, 7110-7113. (e) Rigby, J. H.; Danca, D. M. Tetrahedron Lett. 1997, 38, 4969-4972.
28. For Diels-Alder reaction approaches to B, C, and D ring formation, see: (a) Fortunak, J. M. D.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5679-5682. (b) Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (c) Blagg, B. S. J.; Boger, D. L. Tetrahedron 2002, 58, 6343-6349. (d) Toyata, M.; Komori, C.; Ihara, M. J. Org. Chem. 2000, 65, 7110-7113. (e) Rigby, J. H.; Danca, D. M. Tetrahedron Lett. 1997, 38, 4969-4972.
29. For Diels-Alder reaction approaches to B, C, and D ring formation, see: (a) Fortunak, J. M. D.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5679-5682. (b) Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (c) Blagg, B. S. J.; Boger, D. L. Tetrahedron 2002, 58, 6343-6349. (d) Toyata, M.; Komori, C.; Ihara, M. J. Org. Chem. 2000, 65, 7110-7113. (e) Rigby, J. H.; Danca, D. M. Tetrahedron Lett. 1997, 38, 4969-4972.
30. For Diels-Alder reaction approaches to B, C, and D ring formation, see: (a) Fortunak, J. M. D.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5679-5682. (b) Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (c) Blagg, B. S. J.; Boger, D. L. Tetrahedron 2002, 58, 6343-6349. (d) Toyata, M.; Komori, C.; Ihara, M. J. Org. Chem. 2000, 65, 7110-7113. (e) Rigby, J. H.; Danca, D. M. Tetrahedron Lett. 1997, 38, 4969-4972.
31. Ma, Z.-Z.; Hano, Y.; Nomura, T.; Chen, Y.-J. Heterocycles 1997, 46, 541-546.
32. For recent syntheses, see: (a) Azizian, J.; Mohammadi, A. A.; Ardakani, F.; Karimi, A. R.; Mohammadizadeh, M. R. Heterocycles 2004, 63, 791-795. (b) Cagir, A.; Jones, S. H.; Eisenhauer, B. M.; Gao, R.; Hecht, S. M. Bioorg. Med. Chem. Lett. 2004, 14, 2051-2054. (c) Mhaske, S. B.; Argade, N. P. J. Org. Chem. 2004, 69, 4563-4566 and references therein.
33. For recent syntheses, see: (a) Azizian, J.; Mohammadi, A. A.; Ardakani, F.; Karimi, A. R.; Mohammadizadeh, M. R. Heterocycles 2004, 63, 791-795. (b) Cagir, A.; Jones, S. H.; Eisenhauer, B. M.; Gao, R.; Hecht, S. M. Bioorg. Med. Chem. Lett. 2004, 14, 2051-2054. (c) Mhaske, S. B.; Argade, N. P. J. Org. Chem. 2004, 69, 4563-4566 and references therein.
34. For recent syntheses, see: (a) Azizian, J.; Mohammadi, A. A.; Ardakani, F.; Karimi, A. R.; Mohammadizadeh, M. R. Heterocycles 2004, 63, 791-795. (b) Cagir, A.; Jones, S. H.; Eisenhauer, B. M.; Gao, R.; Hecht, S. M. Bioorg. Med. Chem. Lett. 2004, 14, 2051-2054. (c) Mhaske, S. B.; Argade, N. P. J. Org. Chem. 2004, 69, 4563-4566 and references therein.
35. There have been few reports of intramolecular Povarov reactions; see: (a) Laschat, S.; Lauterwein, J. J. Org. Chem. 1993, 58, 2856-2861. (b) Wölfling, J.; Frank, E.; Schneider, G.; Tietze, L. F. Eur. J. Org. Chem. 1999, 3013-3020. (c) Magomedov, N. A. Org. Lett. 2003, 5, 2509-2512.
36. There have been few reports of intramolecular Povarov reactions; see: (a) Laschat, S.; Lauterwein, J. J. Org. Chem. 1993, 58, 2856-2861. (b) Wölfling, J.; Frank, E.; Schneider, G.; Tietze, L. F. Eur. J. Org. Chem. 1999, 3013-3020. (c) Magomedov, N. A. Org. Lett. 2003, 5, 2509-2512.
37. There have been few reports of intramolecular Povarov reactions; see: (a) Laschat, S.; Lauterwein, J. J. Org. Chem. 1993, 58, 2856-2861. (b) Wölfling, J.; Frank, E.; Schneider, G.; Tietze, L. F. Eur. J. Org. Chem. 1999, 3013-3020. (c) Magomedov, N. A. Org. Lett. 2003, 5, 2509-2512.
38. An intramolecular Diels-Alder reaction has been used to form the B ring of topotecan, via activation of an N-aryl imidate with trimethyloxonium fluoroborate; see: refs 14a and 14b.
39. Stockley, M.; Clegg, W.; Fontana, G.; Golding, B. T.; Martin, N.; Rigoreau, L. J. M.; Smith, G. C. M.; Griffin, R. J. Bioorg. Med. Chem. Lett. 2001, 11, 2837-2841.
40. For leading references on the synthesis of pyridones, see: Carles, L.; Narkunan, K.; Penlou, S.; Rousset, L.; Bouchu, D.; Cuifolini, M. A. J. Org. Chem. 2002, 67, 4304-4308.
41. Ricoh, I.; Halvorsen, K.; Dubrule, C.; Lattes, A. J. J. Org. Chem. 1994, 59, 415-420.
42. Liu, H.; Ko, S.-B.; Josien, H.; Curran, D. P. Tetrahedron Lett. 1995, 36, 8917-8920.
43. Eckert, H. Angew. Chem., Int. Ed. Engl. 1981, 20, 208-210.
44. Usifoh, C. O.; Scriba, G. K. E. Arch. Pharm. Pharm. Med. Chem. 2000, 333, 261-266.
45. Bergman, J.; Brynolf, A. Tetrahedron 1990, 46, 1295-1310.
46. O'Mahony, D. J. R.; Krchnák, V. Tetrahedron Lett. 2002, 43, 939-942.
47. He, F.; Snider, B. B. J. Org. Chem. 1999, 64, 1397-1399.
48. Wang, H.; Ganesan, A. J. Org. Chem. 1998, 63, 2432-2433.
49. Mazurkiewicz, R. Monatsh. Chem. 1989, 120, 973-980.