Enantioselective Total Syntheses of Pentacyclic Homoproaporphine Alkaloids
Liu‐Yang Pu, F. Yang, Ji‐Qiang Chen, Ying Xiong, Huai‐Yu Bin, Jian‐Hua Xie, Qi‐Lin Zhou
Abstract
Herein we report the first enantioselective total syntheses of pentacyclic homoproaporphine alkaloids by means of a route, which includes a tandem retro-oxa-Michael addition and nucleophilic substitution to generate the oxa-benzobicyclco[3.3.1]nonane core structure, a Pictet-Spengler cyclization to construct the fused B and C rings, and sequential Baeyer-Villiger oxidation and pinacol-type cyclization to install the hydroxyl-lactol moiety of D ring. With this unified route, six pentacyclic homoproaporphine alkaloids have been synthesized enantioselectively.
Topics & Concepts
ChemistryEnantioselective synthesisMoietyLactolStereochemistryRing (chemistry)TandemPinacolSquaramideNonaneLactoneOrganic chemistryOrganocatalysisCatalysisComposite materialMaterials scienceTraditional and Medicinal Uses of AnnonaceaeAlkaloids: synthesis and pharmacologyChemical synthesis and alkaloids