115262-25-4Relevant academic research and scientific papers
Use of the Electrophilic Arylation Reaction of Aryl-lead Triacetates in a Sythesis of (+/-)-Lycoramine
Ackland, Darren J.,Pinhey, John T.
, p. 2695 - 2700 (2007/10/02)
A formal total synthesis of (+/-)-lycoramine is reported.The quaternary carbon centre of the alkaloid was produced by a novel electrophilic arylation of the mixture of isomeric vinylogous keto esters (4) and (5) by 2,3-dimethoxyphenyl-lead triacetate.The resulting key intermediate (7c), which was formed in almost quantitative yield, was converted in a straightforward sequence into the formamide (25), from which the alkaloid has been produced previously by a Bischler-Napieralski cyclisation.Functional group protection was only required at one stage in the synthesis.
