作者:José Barluenga、Carlos Mateos、Fernando Aznar、Carlos Valdés
DOI:10.1021/jo049003a
日期:2004.10.1
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
据报道,一种非常简单的方法是制备具有几种环大小的1-氮杂双环生物碱支架。最终的双环结构是通过合成方案构建的,该方案包括(i)在Yb(OTf)3存在的情况下,通过氨基三烯与N -ω-乙烯基酰亚胺之间的亚氨基Diels-Alder反应构建二烯4-哌啶酮体系, (ii)在第一代Grubbs的Ru-络合物催化剂的影响下,这些环状二烯的闭环复分解反应。在此研究过程中,报道了各种多取代的氮杂双环骨架,包括喹oli嗪生物碱的几个实例,并对它们的相对立体化学进行了充分的讨论。