126261-83-4Relevant academic research and scientific papers
The Synthesis of Indolizidine and Quinolizidine Ring Systems by Free Radical Cyclization of 4-Aza-6-methoxycarbonyl-5-hexenyl Radicals
Beckwith, Athelstan L. J.,Westwood, Steven W.
, p. 5269 - 5282 (2007/10/02)
The formation of bicyclic amines by the intramolecular cyclization of 4-aza-6-methoxycarbonyl-5-hexenyl radicals is described.The direct attachment of a nitrogen atom to the double bond changes the electronic nature of the alkene such that the cyclization is less efficient than the all carbon analogue or the other aza-substituted 5-hexenyl cyclizations.The reaction has been used in a short, convenient synthesis of a variety of indolizidines from methyl nicotinate.In addition, the cyclization was used as the key step in a short synthesis of (+/-)-epilupinine from methyl nicotinate.
