Total synthesis of (±)-homoepibatidine

Archives of Pharmacal Research

Volumn 22, Issue 4, 1999, Pages 435-436

  Kim, Yong Hyun ^a   Won, Do Youn ^a   Oh, Chang Young ^a   Lee, Kee Young ^a   Jeong, Jin Hyun ^b   Jung, Young Hoon ^a   Ham, Won Hun ^a  

^a Sungkyunkwan University   (South Korea)

^b Kyung Hee University   (South Korea)

Author keywords

Alkaloids; Analgesics; Palladium; Stereocontrol

Indexed keywords

ANALGESIC AGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; EPIBATIDINE; FUSED HETEROCYCLIC RINGS; PALLADIUM; PYRIDINE DERIVATIVE;

ARTICLE; SYNTHESIS;

ANALGESICS, NON-NARCOTIC; BICYCLO COMPOUNDS, HETEROCYCLIC; INDICATORS AND REAGENTS; PALLADIUM; PYRIDINES;

EID: 0033173592     PISSN: 02536269     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02979073     Document Type: Article

References (11)

1. Bai, D., Xu, R., Chu, G., and Zhu, X. Synthesis of (±)-epibatidine and its analogues. J. Org. Chem., 61, 4600-4606 (1996).
2. Fisher, M., Huang, D. F., Shen, T. Y., and Cuyenet, P. G. Epibatidine, an alkaloid from the poison frog Epipedobabtes tricolor, is a powerful ganglionic depolarizing agent. J.Pharmcol. Exp. Ther., 270, 702-707 (1994).
3. Koren, A. O., Horti, A. G., Mukhin, A. G., Gundisch, D., Kimes, A. S., Dannals, R. F., and London, E. D. 2-, 5-, and 6-halo-3-(2(S)-azetidinylmethoxy)pyridines: synthesis, affinity for nicotinic acetylcholine receptors, and mole-cular modeling. J. Med. Chem., 41, 3690-3698 (1999).
4. Malpass, J. R., Hemmings, D. A., and Wallis, A. L. Synthesis of epibatidine homoloues. Tetrahedron Lett., 37, 3911-3914 (1996).
5. Malpass, J. R., and Cox, C. D. Synthesis of 5- and 6-chloropyridyl-substituted 2-azabicyclo [2.2.1]heptanes; novel epibatidine isomers. Tetrahedron Lett., 40, 1419-1422 (1999).
6. Mann, J., Barbosa, L-C de A. An efficient route to the tropane alkaloids. J. Chem. Soc. Perkin Trans. 1., 787-789 (1992).
7. Pandey, G., Bagul, T. D., Sahoo, A. K. [3+2] Cyclo-addition of nonstabilized azomethine ylides. Stereoselective synthesis of epibatidine and analogues. J. Org. Chem., 63, 760-768 (1998).
8. Qian, C., Li, T., and Shen, T. Y., Libertine-Caraham, L., Eckman, J., Biftu, T., Ip, S. Eur. J. Pharmacol., 250, R13-R14 (1993).
9. Rasmussen, J. R., Slinger, C. J., Kordish, R. J., and Newman-Evans, D. D. Synthesis of deoxy sugars. J. Org. Chem., 46, 4843-4846 (1981).
10. Spande, T. F., Garraffo, H. M., Edwards, M. W., Ych, H. J. C., Pannel, L., and Daly, J. W. Epibatidine:a novel (chloropyridyl)azabicycloheptane with potent analgesic from an ecuadoran poison frog. J. Am. Chem. Soc., 114, 3475-3478 (1992).
11. Zhang C., Gyermek, L., and Trudell, M. L. Synthesis of optically pure epibatidine analogs. Tetrahedron Lett., 38, 5619-5622 (1997).