A Formal Synthesis of (±)-Arborisidine
Liang Huo, Yunxia Yang, Xiaofei Gao, Wei Chen, Xuegong She, Xiao‐Ping Cao
Abstract
Herein, we report a formal synthesis of (±)-arborisidine via the creation of Jiao's intermediate with the critical caged structure. Starting from tryptamine, a Pictet-Spengler cyclization forged the piperidine ring, a Pd-catalyzed indole allylation and ring-closing metathesis protocol afforded a bridged aza-bicyclo[3.3.1]nonane moiety, and an intramolecular N-alkylation closed the final pyrrolidine ring. This study provides a new approach to the unique caged framework of arborisidine and relevant alkaloids.
Topics & Concepts
ChemistryPyrrolidinePiperidineMoietyNonaneTryptamineIntramolecular forceRing (chemistry)StereochemistryRing-closing metathesisIndole testMetathesisBicyclic moleculeAlkylationCatalysisOrganic chemistryPolymerizationBiochemistryPolymerChemical synthesis and alkaloidsSynthetic Organic Chemistry MethodsAdvanced Synthetic Organic Chemistry