Synthesis of epibatidine and analogs thereof

Details Synthesis of epibatidine and analogs thereof Synthesis of epibatidine and analogs thereof

1993-11-12

1996-10-15

Fan, Jane

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546348, C07D40104

Patent

active

055655734

ABSTRACT:
The present invention provides a method to prepare epibatidine or an analog thereof comprising reacting a bicyclic olefin or diene, such as an azanorbornene, with an aryl or heteroaryl halide or triflate in the presence of a catalytic amount of Pd(O) and a formate salt.

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C. A. Broka, "Total Synthesis of Epibatidine," Tet. Letters, 34(20), 3251 (1993).
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S. C. Clayton et al., "A Total Synthesis of (.+-.)-Epibatidine," Tet. Letters, 34(46), 7493 (1993).
E. J. Corey et al., "Stereocontrolled Total Synthesis (+)-(-)-Epibatidine," J. Org. Chem., 58(21), 5600 (1993).
S. R. Fletcher et al., "The Synthesis of (+) and (-)-Epibatidine," J. Chem. Soc., Chem. Commun., 1216 (1993).
D. F. Huang et al., "A Versatile Total Synthesis of Epibatidine and Analogs," Tet. Letters, 34(28), 4477 (1993).
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T. F. Spande et al., "Epibatidine: A Novel (Chloropyridyl)azabicycloheptane with Potent Analgesic Activity from an Ecuadoran Poison Frog," J. Am. Chem. Soc., 114, 3475 (1992).

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