Application of intramolecular enyne metathesis to the synthesis of aza[4.2.1]bicyclics: Enantiospecific total synthesis of (+)-anatoxin-a

Organic Letters

Volumn 6, Issue 8, 2004, Pages 1329-1331

  Brenneman, Jehrod B ^a   Martin, Stephen F ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANATOXIN A; BICYCLO COMPOUND; DEXTRO METHYLPYROGLUTAMATE; GLUTAMIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; NICOTINIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; METHODOLOGY; STEREOCHEMISTRY;

ALKYNES; AZA COMPOUNDS; BACTERIAL TOXINS; BICYCLO COMPOUNDS, HETEROCYCLIC; MARINE TOXINS; MICROCYSTINS; MOLECULAR STRUCTURE; NICOTINIC AGONISTS; PYRROLIDINES; PYRROLIDONECARBOXYLIC ACID; STEREOISOMERISM;

EID: 2542452745     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049631e     Document Type: Article

References (42)

1. Devlin, J. P.; Edwards, O. E.; Gorham, P. R.; Hunter, N. R.; Pike, R. K. Can. J. Chem. 1977, 55, 1367.
2. (a) Carmichael, W. W.; Biggs, D. F.; Gorham, P. R. Science 1975, 187, 542.
3. (b) Spivak, C. E.; Witkop, B.; Albuquerque, E. X. Mol. Pharmacol. 1980, 18, 384.
4. For the most recent syntheses, see: (a) Wegge, T.; Schwarz, S.; Seitz, G. Tetrahedron: Asymmetry 2000, 11, 1405. (b) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309. (c) Aggarwal, V. K.; Humphries, P. S.; Fenwick, A. Angew. Chem., Int. Ed. 1999, 38, 1985. (d) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (e) Oh, C.-Y.; Kim, K.-S.; Ham, W.-H. Tetrahedron Lett. 1998, 39, 2133. For a review of earlier syntheses, see: (f) Mansell, H. L. Tetrahedron 1996, 52, 6025.
5. For the most recent syntheses, see: (a) Wegge, T.; Schwarz, S.; Seitz, G. Tetrahedron: Asymmetry 2000, 11, 1405. (b) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309. (c) Aggarwal, V. K.; Humphries, P. S.; Fenwick, A. Angew. Chem., Int. Ed. 1999, 38, 1985. (d) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (e) Oh, C.-Y.; Kim, K.-S.; Ham, W.-H. Tetrahedron Lett. 1998, 39, 2133. For a review of earlier syntheses, see: (f) Mansell, H. L. Tetrahedron 1996, 52, 6025.
6. For the most recent syntheses, see: (a) Wegge, T.; Schwarz, S.; Seitz, G. Tetrahedron: Asymmetry 2000, 11, 1405. (b) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309. (c) Aggarwal, V. K.; Humphries, P. S.; Fenwick, A. Angew. Chem., Int. Ed. 1999, 38, 1985. (d) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (e) Oh, C.-Y.; Kim, K.-S.; Ham, W.-H. Tetrahedron Lett. 1998, 39, 2133. For a review of earlier syntheses, see: (f) Mansell, H. L. Tetrahedron 1996, 52, 6025.
7. For the most recent syntheses, see: (a) Wegge, T.; Schwarz, S.; Seitz, G. Tetrahedron: Asymmetry 2000, 11, 1405. (b) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309. (c) Aggarwal, V. K.; Humphries, P. S.; Fenwick, A. Angew. Chem., Int. Ed. 1999, 38, 1985. (d) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (e) Oh, C.-Y.; Kim, K.-S.; Ham, W.-H. Tetrahedron Lett. 1998, 39, 2133. For a review of earlier syntheses, see: (f) Mansell, H. L. Tetrahedron 1996, 52, 6025.
8. For the most recent syntheses, see: (a) Wegge, T.; Schwarz, S.; Seitz, G. Tetrahedron: Asymmetry 2000, 11, 1405. (b) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309. (c) Aggarwal, V. K.; Humphries, P. S.; Fenwick, A. Angew. Chem., Int. Ed. 1999, 38, 1985. (d) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (e) Oh, C.-Y.; Kim, K.-S.; Ham, W.-H. Tetrahedron Lett. 1998, 39, 2133. For a review of earlier syntheses, see: (f) Mansell, H. L. Tetrahedron 1996, 52, 6025.
9. For the most recent syntheses, see: (a) Wegge, T.; Schwarz, S.; Seitz, G. Tetrahedron: Asymmetry 2000, 11, 1405. (b) Parsons, P. J.; Camp, N. P.; Edwards, N.; Sumoreeah, L. R. Tetrahedron 2000, 56, 309. (c) Aggarwal, V. K.; Humphries, P. S.; Fenwick, A. Angew. Chem., Int. Ed. 1999, 38, 1985. (d) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057. (e) Oh, C.-Y.; Kim, K.-S.; Ham, W.-H. Tetrahedron Lett. 1998, 39, 2133. For a review of earlier syntheses, see: (f) Mansell, H. L. Tetrahedron 1996, 52, 6025.
10. (a) Karig, G.; Large, J. M.; Sharples, C. G. V.; Sutherland, A.; Gallagher, T.; Wonnacott, S. Biorg. Med. Chem. Lett. 2003, 13, 2825.
11. (b) Sutherland, A.; Gallagher, T.; Sharples, C. G. V.; Wonnacott, S. J. Org. Chem. 2003, 68, 2475.
12. (c) Gohlke, H.; Schwarz, S.; Gündisch, D.; Tilotta, M. C.; Weber, A.; Wegge, T.; Seitz, G. J. Med. Chem. 2003, 46, 2031.
13. (d) Sharples, C. V. G.; Karig, G.; Simpson, G. L.; Spencer, J. A.; Wright, E.; Millar, N. S.; Wonnacott, S.; Gallagher, T. J. Med. Chem. 2002, 45, 3235.
14. (e) Gohlke, H.; Gündisch, D.; Schwarz, S.; Seitz, G.; Tilotta, M. C.; Wegge, T. J. Med. Chem. 2002, 45, 1064.
15. (f) Gündisch, D.; Kämpchen, T.; Schwarz, S.; Seitz, G.; Siegl, J.; Wegge, T. Biorg. Med. Chem. 2002, 10, 1.
16. (g) Sharples, C. V. G.; Kaiser, S.; Soliakov, L.; Marks, M. J.; Collins, A. C.; Washburn, M.; Wright, E.; Spencer, J. A.; Gallagher, T.; Whiteaker, P.; Wonnacott, S. J. Neurosci. 2000, 20, 2783.
17. (h) Wright, E.; Gallagher, T.; Sharples, C. V. G.; Wonnacott, S. Biorg. Med. Chem. Lett. 1997, 7, 2867.
18. (i) Sardina, F. J.; Howard, M. H.; Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 4654.
19. (a) Neipp, C. E.; Martin, S. F. J. Org. Chem. 2003, 68, 8867.
20. (b) Neipp, C. E.; Martin, S. F. Tetrahedron Lett. 2002, 43, 1779.
21. For additional examples of bridged azabicycles prepared by RCM, see: (a) Itoh, T.; Yamazaki, N.; Kibayashi, C. Org. Lett. 2002, 4, 2469. (b) Bamford, S. J.; Goubitz, K.; van Lingen, H. L.; Luker, T.; Schenk, H.; Hiemstra, H. J. Chem. Soc., Perkin Trans, I 2000, 345. (c) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255. (d) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (e) Pandit, U. K.; Borer, B. C.; Bieräugel, H. Pure Appl. Chem. 1996, 68, 659.
22. For additional examples of bridged azabicycles prepared by RCM, see: (a) Itoh, T.; Yamazaki, N.; Kibayashi, C. Org. Lett. 2002, 4, 2469. (b) Bamford, S. J.; Goubitz, K.; van Lingen, H. L.; Luker, T.; Schenk, H.; Hiemstra, H. J. Chem. Soc., Perkin Trans, I 2000, 345. (c) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255. (d) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (e) Pandit, U. K.; Borer, B. C.; Bieräugel, H. Pure Appl. Chem. 1996, 68, 659.
23. For additional examples of bridged azabicycles prepared by RCM, see: (a) Itoh, T.; Yamazaki, N.; Kibayashi, C. Org. Lett. 2002, 4, 2469. (b) Bamford, S. J.; Goubitz, K.; van Lingen, H. L.; Luker, T.; Schenk, H.; Hiemstra, H. J. Chem. Soc., Perkin Trans, I 2000, 345. (c) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255. (d) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (e) Pandit, U. K.; Borer, B. C.; Bieräugel, H. Pure Appl. Chem. 1996, 68, 659.
24. For additional examples of bridged azabicycles prepared by RCM, see: (a) Itoh, T.; Yamazaki, N.; Kibayashi, C. Org. Lett. 2002, 4, 2469. (b) Bamford, S. J.; Goubitz, K.; van Lingen, H. L.; Luker, T.; Schenk, H.; Hiemstra, H. J. Chem. Soc., Perkin Trans, I 2000, 345. (c) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255. (d) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (e) Pandit, U. K.; Borer, B. C.; Bieräugel, H. Pure Appl. Chem. 1996, 68, 659.
25. For additional examples of bridged azabicycles prepared by RCM, see: (a) Itoh, T.; Yamazaki, N.; Kibayashi, C. Org. Lett. 2002, 4, 2469. (b) Bamford, S. J.; Goubitz, K.; van Lingen, H. L.; Luker, T.; Schenk, H.; Hiemstra, H. J. Chem. Soc., Perkin Trans, I 2000, 345. (c) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255. (d) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (e) Pandit, U. K.; Borer, B. C.; Bieräugel, H. Pure Appl. Chem. 1996, 68, 659.
26. Alternatively, 4 may be prepared from D-pyroglutamic acid. See: Pfaltz, A.; Leutenegger, U.; Siegmann, K.; Fritschi, H.; Keller, W.; Krathy, C. Helv. Chim. Acta 1988, 71, 1541.
27. For related examples of reactions of organometallic reagents with N-alkoxycarbonyl lactams, see: (a) Giovannini, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1989, 54, 228. (b) Ohta, T.; Hosoi, A.; Kimura, T.; Nozoe, S. Chem. Lett. 1987, 2091.
28. For related examples of reactions of organometallic reagents with N-alkoxycarbonyl lactams, see: (a) Giovannini, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1989, 54, 228. (b) Ohta, T.; Hosoi, A.; Kimura, T.; Nozoe, S. Chem. Lett. 1987, 2091.
29. In the absence of TMEDA, ketoamide 6 was obtained in only 45% yield together with substantially larger quantities of 4.
30. 6).
31. Rudolph, A.; Machauer, R.; Martin, S. F. Unpublished results.
32. (a) Mota, A. J.; Chiaroni, A.; Langlois, N. Eur. J. Org. Chem. 2003, 21, 4187.
33. (b) Li, H.; Sakamoto, T.; Kikugawa, Y. Tetrahedron Lett. 1997, 38, 6677.
34. (c) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373.
35. (d) Jegham, S.; Das, B. Tetrahedron Lett. 1989, 30, 2801.
36. (e) Shiosaki, K.; Rapoport, H. J. Org. Chem. 1985, 50, 1229.
37. (a) Ohira, S. Synth. Commun. 1989, 19, 561.
38. (b) Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521.
39. Petersen, J. S.; Fels, G.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 4539 and references therein.
40. Stevens, D. K.; Krieger, R. I. Toxicon 1991, 29, 167.
41. Koskinen, A. M. P.; Rapoport, H. J. Med. Chem. 1985, 28, 1301.
42. 24D +43.2 (c 0.676, abs. EtOH).