An approach to the skeleton of the securinega alkaloids. The total synthesis of (±)-securinine

Organic Letters

Volumn 3, Issue 5, 2001, Pages 703-706

  Liras, Spiros ^a   Davoren, Jennifer E ^a,b   Bordner, Jon ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

^b UNIVERSITY OF SAINT JOSEPH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID RECEPTOR BLOCKING AGENT; ALKALOID; AZEPINE DERIVATIVE; CENTRAL STIMULANT AGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FUSED HETEROCYCLIC RINGS; LACTONE; PIPERIDINE DERIVATIVE; SECURININE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CRYSTALLIZATION; MEDICINAL PLANT; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; AZEPINES; CENTRAL NERVOUS SYSTEM STIMULANTS; CRYSTALLIZATION; GABA ANTAGONISTS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDICATORS AND REAGENTS; LACTONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PIPERIDINES; PLANTS, MEDICINAL; STEREOISOMERISM;

EID: 0035826385     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0070482     Document Type: Article

References (26)

1. Murav'eva, V. I.; Ban'kovskii, A. I. Dokl. Akad. Nauk SSSR 1956, 110, 998.
2. (a) Satoda, I.; Murayama, M.; Tsuji, Y.; Yoshii, E. Tetrahedron Lett. 1962, 3, 1199.
3. (b) Nakano, T.; Yang, T. H.; Terao, S. Tetrehedron 1963, 19, 609.
4. Imado, S.; Shiro, M.; Horii, Z. Chem. Pharm. Bull. 1965, 13, 643.
5. Horii, Z.; Hanaoka, M.; Yaamawaki, Y.; Tamura, Y.; Saito, S.; Shigematsu, N.; Kotera, K.; Yoshikawa, H.; Sato, Y.; Nakai, H.; Sugimoto, N. Tetrahedron 1967, 23, 1165.
6. Honda, T.; Namiki, H.; Kudoh, M.; Watanabe, N.; Nagase, H.; Mizutani, H. Tetrahedrom Lett. 2000, 41, 5927.
7. For examples, see: (a) Cote, R.; Bouchard, P.; Couture, Y.; Furstoss, R.; Waegell, B.; Lessard, J. Heterocycles 1989, 28 (2), 987.
8. (b) Wanner, K. T. Eur. J. Pharm. Sci. 1994, 2, 62.
9. Beutler, J. A.; Karbon, E. W.; Brubaker, A. N.; Malik, R.; Curtis, D. R.; Enna, S. J. Brain Res. 1985, 330 (1), 135
10. Martin, S. F.; Bur, S. K. Tetrahedron Lett. 1997, 38, 7641.
11. Pilli, R. A.; Dias, L. C. Synth. Commun. 1991, 21 (21), 2213.
12. For reviews, see: (a) Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929.
13. (b) Martin, S. F. Pure Appl. Chem. 1997, 69, 571.
14. For selected examples, see: (a) Martin, S. F.; Barr, K. J.; Smith, D. W.; Bur, S. K. J. Am. Chem. Soc. 1999, 121, 6990.
15. (b) Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450.
16. (c) Martin, S. F.; Bur, S. K. Tetrahedron Lett. 1997, 38, 7641.
17. For a rationale regarding the diastereoselectivity of silyloxyfuran additions to related cyclic iminium ions, see: Martin, S. F.; Bur, S. K. Org. Lett. 2000, 2, 3445.
18. (a) Hua, D. H.; Sinai-Zingde, G.; Venkataraman, S. J. Am. Chem. Soc. 1985, 107, 4088.
19. (b) Hua, D. H., Venkataraman, S.; Coulter; M. J.; Sinai-Zingde, G. J. Org. Chem. 1987, 52, 719.
20. For recent reviews regarding applications of the ring closing metathesis reaction, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
21. (b) Pandit, U. K.; Overkleeft, H. S.; Borer, B. C.; Bieraugel, H. Eur. J. Org. Chem. 1940, 5, 959.
22. (c) Wright, D. L. Curr. Org. Chem. 1999, 3, 211.
23. (d) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75.
24. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073.
25. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
26. Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153.