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Synthesis of trans-2,6-dialkylpiperidines by intramolecular amidomercuration
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1984
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Medicinal ChemistryBioorganic ChemistryEngineeringBiochemistryNatural SciencesVenomicsPeptide SynthesisOrganic ChemistryIntramolecular AmidomercurationSolenopsin ASodium BorohydridePharmacologyPharmaceutical ChemistrySynthetic ChemistryBiomolecular EngineeringNeuropeptides
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.