Tetrahedron p. 5391 - 5400 (1991)
Update date:2022-08-03
Topics:
Rosen
Guarino
The discovery and selective synthesis of a novel and highly potent serotonin-3 receptor ligand, 4-amino-5-chloro-2-methoxy-N-(1-azabicyclo[2.2.2]-oct-2-enyl-2-methyl) benzamide (4) are described. The key step in the preparation of 4 involves an unusual example of a kinetically controlled displacement to provide a thermodynamically disfavored allylic azide isomer. This azide is a precursor to 2-aminomethyl-1-azabicyclo[2.2.2]oct-2-ene, a convergent intermediate for the synthesis of analogs related to 4.
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Doi:10.1021/acs.jnatprod.6b00670
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(2011)
