An efficient and enantioselective approach to the azaspirocyclic core of alkaloids: Formal synthesis of halichlorine and pinnaic acid

Journal of Organic Chemistry

Volumn 70, Issue 13, 2005, Pages 4954-4961

  Zhang, Hong Lu ^a   Zhao, Gang ^a   Ding, Yu ^a   Wu, Bin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; CARBON; CATALYSIS; CONDENSATION; MOLECULAR STRUCTURE; NITROGEN; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVE APPROACH; LIPASE; PINNAIC ACID;

ORGANIC COMPOUNDS;

4 [7 (2 HYDROXY 1'' METHYL ETHYL) 6' TRIFLUOROACETYL 6' AZA 5' SPIRO[4.5]DEC 1' YL] 2 METHYL BUT 2E ENOIC ACID ETHYL ESTER; ALKALOID; ALPHA METHYLENE; CARBENE; CARBON; CYCLOPENTANE DERIVATIVE; HALICHLORINE; KETONE; LACTONE; NITRONE; PINNAIC ACID; PIPERIDINE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; METHYLATION; MICHAEL ADDITION; POLYMERIZATION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

ALKALOIDS; AZA COMPOUNDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 20844447698     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo047882v     Document Type: Article

References (46)

1. Kuramoto, M.; Tong, C.; Yamada, K.; Chiba, T.; Hayashi, Y.; Uemura, D. Tetrahedron Lett. 1996, 37, 3867.
2. Chou, T.; Kuramoto, M.; Otani, Y.; Shikano, M.; Yazawa, K.; Uemura, D. Tetrahedron Lett. 1996, 37, 3871.
3. Postigo, A. A.; Teixido, J.; Sanchezmadrid, F. Res. Immunol. 1993, 144, 723.
4. Nevalainen, T. J. Clin. Chem. (Washington, DC) 1993, 39, 2453.
5. Recent synthetic works on Pinnaic acid and Halichlorine: (a) Keen, S. P.; Weinreb, S. M. J. Org. Chem. 1998, 63, 6739.
6. (b) Martin-Lopez, M. J.; Bermejo, F. Tetrahedron 1998, 54, 12379.
7. (c) Lee, S.; Zhao, Z. S. Org. Lett. 1999, 1, 681.
8. (d) Lee, S.; Zhao, Z. S. Tetrahedron Lett. 1999, 40, 7921.
9. (e) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1999, 40, 8503.
10. (f) Koviach, J. L.; Forsyth, C. J. Tetrahedron Lett. 1999, 40, 8529.
11. (g) Wright, D. L.; Schulte, J. P., II; Page, M. A. Org. Lett. 2000, 2, 1847.
12. (h) Shindo, M.; Fukuda, Y.; Shishido, K. Tetrahedron Lett. 2000, 41, 929.
13. (i) Yokota, W.; Shindo, M.; Shishido, K. Heterocycles 2001, 54, 871.
14. (j) Ciblat, S.; Canet, J. L.; Troin, Y. Tetrahedron Lett. 2001, 42, 4815.
15. (k) Ito, T.; Yamazaki, N.; Kibayashi, C. Synlett. 2001, 1506.
16. (l) White, J. D.; Blakemore, P. R.; Korf, E. A.; Yokochi, A. F. T. Org. Lett. 2001, 3, 413.
17. (m) Fenster, M. D. B.; Patrick, B. O.; Dake, G. R. Org. Lett. 2001, 3, 2109.
18. (n) Taber, D. F.; Mitten, J. V. J. Org. Chem. 2002, 67, 3847.
19. (o) Hayakawa, I.; Arimoto, H.; Uemura, D. Heterocycles 2003, 59, 441.
20. (p) Matsumura, Y.; Aoyagi, S.; Kibayashi, C. Org Lett. 2003, 5, 3249.
21. (q) Matsumura, Y.; Aoyagi, S.; Kibayashi, C. Org Lett. 2004, 6, 965.
22. (r) Takasu, K.; Ohsato, H.; Ihara, M. Org Lett. 2003, 5, 3017.
23. (a) Trauner, D.; Schwarz, J. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1999, 38, 3542.
24. (b) Trauner, D.; Danishefsky, S. J. Tetrahedron left. 1999, 40, 6513.
25. (a) Trauner, D.; Churchill, D. G.; Danishefsky, S. J. Helv. Chim. Acta 2000, 83, 2344.
26. (d) Carson, M. W.; Kim, G.; Hentemann, M. F.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4450.
27. (e) Carson, M. W.; Kim, G.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4453.
28. Christie, H. S.; Heathcock, C. H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12079-12084
29. Goodman, L.; Benitez, A.; Baker, B. R. J. Am. Chem. Soc. 1958, 80, 1680.
30. Grigsby, W. E.; Hind, J.; Chanley, J.; Westheimer, F. H. J. Am. Chem. Soc. 1942, 64, 2606.
31. Krapcho, A. P. Synthesis 1982, 805.
32. Hashimoto, S.; Miyazaki, Y.; Ikegami, S. Synth. Commun. 1992, 22, 2717.
33. (a) Iffland, D. C.; Criner, G. X. J. Am. Chem. Soc. 1953, 75, 4047.
34. (b) Barners, M. W. J. Org. Chem. 1976, 41, 733.
35. (c) Corey, E. J.; Estreicher, H. Tetrahedron Lett. 1980, 21, 1117.
36. (d) Waters, T. R.; Zajac, W. W.; Woods, J. M. J. Org. Chem. 1991, 56, 316.
37. (e) Marchand, A. P.; Sharma, R.; Zope, U. R. J. Org. Chem. 1993, 58, 759.
38. Gardiner, J. M.; Bryce, M. R.; Bates, P. A.; Hursthouse, M. B. J. Org. Chem. 1990, 55, 1261.
39. Tarnchompoo, B.; Thebtaranonth, Y. Tetrahedron Lett. 1984, 25, 5567.
40. Smith, A. B., III; Condon, S. M.; Mccauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 947.
41. (a) Lloyd, D. H.; Nichols, D. E. J. Org. Chem. 1986, 51, 4294.
42. (b) Ganem, B.; Osby, J. O. Chem. Rev. 1986, 764.
43. (a) Stork, G.; Niu, D.; Fujimoto, A.; Koft, E. R.; Balkovec, J. M.; Tata, J. R. J. Am. Chem. Soc. 2001, 123, 3239.
44. (b) Overman, L. E.; Lesuisse, D.; Hashimoto, M. J. Am. Chem. Soc. 1983, 105, 5373.
45. Yamada, K.; Kishikawa, K.; Yamamoto, M. J. Org. Chem. 1987, 52, 2327.
46. Caldwell, C. G.; Rupprecht, K. M.; bondy, S. S.; Davis, A. A. J. Org. Chem. 1990, 55, 2355.