Regiospecific, Enantiospecific Total Synthesis of the 12-Alkoxy- Substituted Indole Alkaloids, (+)-12-Methoxy-Na-methylvellosimine, (+)-12-Methoxyaffinisine, and (-)-Fuchsiaefoline

Organic Letters

Volumn 6, Issue 2, 2004, Pages 249-252

  Zhou, Hao ^a   Liao, Xuebin ^a   Cook, James M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

12 METHOXY N A METHYLVELLOSIMINE; 12 METHOXYAFFINISINE; 7 METHOXY DEXTRO TRYPTOPHAN; ALCOHOL DERIVATIVE; ESTER; FUCHSIAEFOLINE; INDOLE ALKALOID; PALLADIUM; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CROSS COUPLING REACTION; DRUG SYNTHESIS; PICTET SPENGLER REACTION; STEREOSPECIFICITY;

EID: 0842306887     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0362212     Document Type: Article

References (35)

1. Chatterjee, A.; Bandyopadhyay, S. Ind. J. Chem. 1979, 18B, 87.
2. Amer, M. M. A.; Court, W. E. Planta Med. 1980, Suppl., 8.
3. Feng, X. Z.; Fu, F. Y. Acta Pharm. Sin. 1981, 16, 510.
4. Sierra, P.; Novotny, L.; Samek, Z.; Budesinsky, M.; Dolejs, L.; Blaha, K. Collect. Czech. Chem. Commun. 1982, 47, 2912.
5. Lin, M.; Yang, B. Q.; Yu, D. Q. Acta Pharm. Sin. 1986, 21, 114.
6. Banerji, J.; Das, B.; Chakrabarti, R.; Shoolery, J. N. Ind. J. Chem. 1987, 26B, 709.
7. Ponglux, D.; Wongseriprpatana, S.; Subhadhirasakul, S.; Takayama, H.; Yokota, M.; Ogata, K.; Phisalaphong, C.; Aimi, N.; Sakai, S. J. Chem. Soc., Perkin Trans. 1 1989, 5075.
8. Arthur, H. R.; Johns, S. R.; Lamberton, J. A.; Loo, S. N. Aust. J. Chem. 1968, 21, 1399.
9. Braga, R. M.; Reis, F. A. M. Phytochemistry 1987, 26, 833.
10. Kato, L.; Braga, R. M.; Koch, I.; Kinoshita, L. S. Phytochemistry 2002, 60, 315.
11. Li, J.; Wang, T.; Yu, P.; Peterson, A.; Weber, R.; Soerens, D.; Grubisha, D.; Bennett, D.; Cook, J. M. J. Am. Chem. Soc. 1999, 121, 6998.
12. Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
13. Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507.
14. Ma, C.; Liu, X.; Li, X.; Flippen-Anderson, J.; Yu, S.; Cook, J. M. J. Org. Chem. 2001, 66, 4525.
15. (a) Cox, E. D.; Hamker, L. K.; Li, J.; Yu, P.; Czerwinski, K. M.; Deng, L.; Bennett, D. W.; Cook, J. M.; Watson, W. H.; Krawiec, M. J. Org. Chem. 1997, 62, 44.
16. (b) Zhang, L. H.; Trudell, M. L.; Hollinshead, S. P.; Cook, J. M. J. Am. Chem. Soc. 1989, 111, 8263.
17. (c) Zhang, L. H.; Cook, J. M. Heterocycles 1988, 27, 2795.
18. (d) Zhang, L. H.; Gupta, A. G.; Cook, J. M. J. Org. Chem. 1989, 54, 4708.
19. Piers, E.; Marais, P. C. J. Org. Chem. 1990, 55, 3454.
20. Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11.
21. Birman, V. B.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 7219.
22. Wang, T.; Cook, J. M. Org. Lett. 2000, 2, 2057.
23. Solé, D.; Peidró, E.; Bonjoch, J. Org. Lett. 2000, 2, 2225.
24. Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587.
25. Solé, D.; Diab, F.; Bonjoch, J. J. Org. Chem. 2003, 68, 5746.
26. Yamada, S.; Morizano, D.; Yamamoto, K. Tetrahedron Lett. 1992, 33, 4329.
27. Yu, J.; Wang, T.; Liu, X.; Deschamps, J.; Flippen-Anderson, J.; Liao, X. ; Cook, J. M. J. Org. Chem. 2003, 68, 7565.
28. Yamazaki, N.; Dokoshi, W.; Kibayashi, C. Org. Lett. 2001, 3, 193.
29. (a) Bartoli, G.; Palmieri, G.; Bosco, M.; Dalpozzo, R. Tetrahedron Lett. 1989, 30, 2129.
30. (b) Dobbs, A. J. Org. Chem. 2001, 66, 638.
31. (c) Dobson, D.; Todd, A.; Gilmore, J. Synth. Commun. 1991, 21, 611.
32. (d) Dobson, D.; Gilmore, J.; Long, D. A. Synlett 1992, 79.
33. (a) Deng, H.; Jung, K.; Liu, T.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 9032.
34. (b) Pellegrin, C.; Weber, M.; Borschberg, H. Helv. Chim. Acta. 1996, 79, 151.
35. (c) Taniguchi, M.; Anjiki, T.; Nakagawa, M.; Hino, T. Chem. Pharm. Bull. 1984, 32, 2544.