Abstract
Total synthesis of (±)-homoepibatidine (2), which contains the 8-azabicyclo[3.2.1] octane ring system, was achieved by using palladium-catalyzed Heck-type coupling reaction from3.
References Cited
Bai, D., Xu, R., Chu, G., and Zhu, X. Synthesis of (±)-epibatidine and its analogues.J. Org. Chem., 61, 4600–4606 (1996).
Fisher, M., Huang, D. F., Shen, T. Y., and Guyenet, P. G. Epibatidine, an alkaloid from the poison frogEpipedobabtes tricolor, is a powerful ganglionic depolarizing agent.J. Pharmcol. Exp. Ther., 270, 702–707 (1994).
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).
Malpass, J. R., Hemmings, D. A., and Wallis, A. L. Synthesis of epibatidine homoloues.Tetrahedron Lett., 37, 3911–3914 (1996).
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).
Mann, J., Barbosa, L-C de A. An efficient route to the tropane alkaloids.J. Chem. Soc. Perkin Trans. 1, 787–789 (1992).
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).
Qian, C., Li, T. and Shen, T. Y., Libertine-Garaham, L., Eckman, J., Biftu, T., Ip, S.Eur J. Pharmacol., 250, R13-R14 (1993).
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).
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).
Zhang C., Gyermek, L. and Trudell, M.L., Synthesis of optically pure epibatidine analogs.Tetrahedron Lett., 38, 5619–5622 (1997).
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Kim, YH., Won, DY., Oh, CY. et al. Total synthesis of (±)-homoepibatidine. Arch Pharm Res 22, 435–436 (1999). https://doi.org/10.1007/BF02979073
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DOI: https://doi.org/10.1007/BF02979073