Intramolecular amidomercuration of N-methoxycarbonyl-6-aminohept-1-ene and reaction of the resulting organomercurial with sodium borohydride in the presence of acrylonitrile or decen-3-one has been used to prepare trans-2,6-dialkylpiperidines, including solenopsin A, a constituent of the venom of the fire-ant.
W. Carruthers, M. J. Williams and M. T. Cox, J. Chem. Soc., Chem. Commun., 1984, 1235 DOI: 10.1039/C39840001235
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