Efficient synthesis of fused bicyclic glutarimides. Its application to (±)-alloyohimbane and louisianin D

Organic Letters

Volumn 8, Issue 14, 2006, Pages 3033-3035

  Chen, Hung Wei ^a   Hsu, Ru Ting ^b   Chang, Meng Yang ^c   Chang, Nein Chen ^a  

^a NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

^b SHU ZEN COLLEGE OF MEDICINE AND MANAGEMENT   (Taiwan)

^c NATIONAL UNIVERSITY OF KAOHSIUNG   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLOYOHIMBANE; ALLYL COMPOUND; ESTER; FUSED HETEROCYCLIC RINGS; GLUTARIMIDE; LOUISIANIN D; PIPERIDONE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALLYL COMPOUNDS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; ESTERS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PIPERIDONES; PYRIDINES; STEREOISOMERISM;

EID: 33746584370     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060958k     Document Type: Article

References (30)

1. (a) Frederlesen, S. M.; Stermitz, F. R. J. Nat. Prod. 1996, 59, 41.
2. (b) Stefanska, A. L.; Cassel, R.; Ready, S. J.; Warr, S. R. J. Antibiot. 2000, 53, 357.
3. (c) Nakamura, M.; Kido, K.; Kinjo, J.; Nohara, T. Phytochemistry 2000, 53, 253.
4. (d) Nakamura, M.; Chi, Y.-M.; Yan, W.-M.; Yonezawa, A.; Nakagugi, Y.; Toyokichi, Y.; Hashimoto, F.; Kinjo, J.; Nohara, T.; Sakurada, S. Planta Med. 2001, 67, 114.
5. (e) Skaltsounis, A.-L.; Michel, S.; Tillequin, F.; Koch, M.; Pusset, J.; Chauviere, G. Helv. Chim. Acta 1985, 68, 1679.
6. (f) Cook, C. E.; Wani, M. C.; Jump, J. M.; Jee, Y. M.; Fail, P. A. J. Med. Chem. 1995, 38, 753.
7. (g) Ho, H. Y.; Chow, Y. S. J. Chem. Ecol. 1993, 19, 39.
8. (h) Torsell, K.; Wahlberg, K. Acta Chem. Scand. 1967, 21, 53.
9. (i) Scott, J. A.; Crews, F. T. J. Pharmacol. Exp. Ther. 1983, 224, 640.
10. For pyridines, see: (a) Jones, K.; Escudero-Hernandez, M. L. Tetahedron 1998, 54, 2275.
11. (b) John, K.; Fiumana, A.; Escudero-Hernandez, M. L. Tetrahedron 2000, 56, 397.
12. For piperidines, see: (c) Hong, B.-C.; Gupta, A. K.; Wu, M.-F.; Liao, J.-H.; Lee, G.-H. Org. Lett. 2003, 5, 1689.
13. (d) Gunter, M.; Gais, H.-J. J. Org. Chem. 2003, 68, 8037.
14. For δ-lactams, see: (e) Li, T.-T.; Lesko, P.; Ellison, R. H.; Subramanian, N.; Fried, J. H. J. Org. Chem. 1981, 46, 111.
15. (f) Gracias, V.; Frank, K. E.; Milligan, G. L.; Aube, J. Tetrahedron 1997, 48, 16241.
16. For 2-pyridones, see: (g) Yamamoto, Y.; Takagish, H.; Itoh, K. Org. Lett. 2001, 3, 2117.
17. Chang, M.-Y.; Chang, B.-R.; Tai, H.-M.; Chang, N.-C. Tetahedron Lett. 2000, 41, 10273.
18. (a) Bergmeier, S. C.; Seth, P. P. J. Org. Chem. 1999, 64, 3237.
19. (b) Beierle, J. M.; Osimboni, E. B.; Metallinos, C.; Zhao, Y.; Kelly, T. R. J. Org. Chem. 2003, 68, 4970.
20. (c) Kogure, N.; Nishiya, C.; Kitajima, M.; Takayama, H. Tetahedron Lett. 2005, 46, 5857.
21. (a) Sparks, S. M.; Shea, K. J. Tetahedron Lett. 2000, 41, 6721.
22. (b) Aube, J.; Wang, Y. G.; Hammond, M.; Tanol, M.; Takusagawa, F.; Vandervelde, D. J. J. Am. Chem. Soc. 1990, 112, 4879.
23. Takamatsu, S.; Kim, Y.-P.; Hayashi, M.; Furuhata, K.; Takayanagi, H.; Komiyama, K.; Woodruff, H. B.; Omura, S. J. Antibiot. 1995, 48, 1090.
24. Chang, B.-R.; Chen, C.-Y.; Chang, N.-C. Tetrahedron Lett. 2002, 43, 3233.
25. Pampin, M. C.; Estevez, J. C.; Estevez, R. J.; Maestro, M.; Castedo, L. Tetrahedron 2003, 59, 7231.
26. (a) Boch, M.; Korth, T.; Nelke, J. M.; Pike, D.; Radunz, H.; Winterfeldt, E. Chem. Ber. 1972, 105, 2126.
27. (b) Tang, C. S. F.; Morrow, C. J.; Rapoport, H. J. Am. Chem. Soc. 1975, 97, 159.
28. (c) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611.
29. (d) Ragan, J. A.; Jones, B. P.; Meltz, C. N.; Teixeira, J. J., Jr. Sythesis 2002, 4, 483.
30. (e) Stork, G.; Fujimoto, D. N. A.; Koft, E. R.; Balkovec, J. M.; Tata, J. R.; Dake, G. R. J. Am. Chem. Soc. 2001, 123, 3239.