A straightforward and versatile synthetic approach to 1-azabicyclic alkaloids

J Barluenga, C Mateos, F Aznar…

Index: Barluenga, Jose; Mateos, Carlos; Aznar, Fernando; Valdes, Carlos Journal of Organic Chemistry, 2004 , vol. 69, # 21 p. 7114 - 7122

Full Text: HTML

Citation Number: 16

Abstract

A very straightforward route to 1-azabicyclo alkaloid scaffolds with several ring sizes is reported. The final bicyclic structures were built through a synthetic scheme that involved (i) the construction of dienic 4-piperidone systems by an imino-Diels-Alder reaction between aminotrienes and N-ω-vinylimines, in the presence of Yb (OTf) 3, and (ii) the ring-closing metathesis reaction of these cyclic dienes, under the influence of the first-generation ...