piperidines has been researched along with butenolide* in 2 studies
2 other study(ies) available for piperidines and butenolide
| Article | Year |
|---|---|
Divergent synthetic strategy leading to structurally diverse pyrrolidines and piperidines from common gamma-aminoalkyl butenolide and aldehyde precursors.
Condensation between aldehydes and the secondary amino function of 5-(aminoalkyl)furan-2(5H)-ones, obtained by the silyloxyfuran dienolate addition to imine-type derivatives, produces either aminoalkylbenzotriazoles or 1,2,3,4-tetrahydropyridines. The former can be reduced with SmI2 to generate alpha-aminoalkyl radicals that are trapped by the alpha,beta-unsaturated lactone moiety yielding substituted pyrrolidines diastereoselectively, while catalytic hydrogenation of the latter affords isomeric piperidine analogues. Alternatively, SmI2-promoted reduction of tetrahydropyridines in the presence of acid also leads to intermediate alpha-aminoalkyl radicals that participate in inter- or intramolecular olefin addition reactions. Further manipulation of the lactone functionality in various ways gives access to a number of interesting derivatives based upon either a pyrrolidine or a piperidine structural motif. As a result, a high degree of structural diversity is obtained in a few steps starting from a common set of simple materials. Topics: 4-Butyrolactone; Aldehydes; Cyclization; Free Radicals; Molecular Structure; Piperidines; Pyrrolidines; Stereoisomerism | 2006 |
Biomimetic total synthesis of (+)-himbacine.
On treatment with trifluoroacetic acid butenolide 14 undergoes N-Boc deprotection and condensation followed by an iminium ion activated intramolecular Diels-Alder cycloaddition to give the (+)-himbacine precursor 11 on reductive work up. Compound 11 was converted into (+)-himbacine in four synthetic steps. [reaction: see text] Topics: 4-Butyrolactone; Aldehydes; Alkaloids; Alkenes; Furans; Models, Molecular; Naphthalenes; Piperidines; Stereoisomerism; Trifluoroacetic Acid | 2005 |