Total Synthesis of (±)-Spiroaxillarone A
Minjian Liao, Xiangxin Li, Yajuan Zheng, Zhixiang Xie
Abstract
Spiroaxillarone A, a novel and unique spirocyclic dinaphthalene natural product with significant antimalarial activity, was regioselectively synthesized from tetrahydrocurcumin in five steps with an overall 10% yield. Key features of the synthesis involved an oxidized free radical cycloaddition to build the spiro ring central skeleton and an oxidized dehydrogenation to introduce two double bonds via enol silicon ether from diketones.
Topics & Concepts
DehydrogenationCycloadditionYield (engineering)Natural productRing (chemistry)ChemistryEtherEnol etherEnolTotal synthesisSkeleton (computer programming)StereochemistryOrganic chemistryCatalysisComputer scienceMaterials scienceProgramming languageMetallurgyMarine Sponges and Natural ProductsTraditional and Medicinal Uses of AnnonaceaeAlkaloids: synthesis and pharmacology