- Synthesis of trans-2,6-Dialkylpiperidines by Intramolecular Amidomercuriation and by 1,3-Cycloaddition of Alkenes to 2-Methyl-2,3,4,5-tetrahydropyridine Oxide
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Intramolecular amidomercuriation of methyl N-hept-6-en-2-ylcarbamate and reaction of the resulting organomercurial with sodium borohydride in the presence of acrylonitrile or dec-1-en-3-one has been used to prepare trans-2,6-dialkylpiperidines.A more stereoselective route lies in the cycloaddition of alkenes to 2-alkyl-2,3,4,5-tetrahydropyridine oxides followed by reductive cleavage of the resulting perhydroisoxazolopyridine.Both procedures are illustrated by synthesis of the fire ant-venom alkaloid, solenopsin A.
- Adams, David R.,Carruthers, William,Williams, Michael J.,Crowley, Patrick J.
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p. 1507 - 1513
(2007/10/02)
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