Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade
James A. Rossi‐Ashton, Aimee K. Clarke, Richard J. K. Taylor, William P. Unsworth
Abstract
The polycyclic core of the akuammiline alkaloids can be synthesized from simple tryptamine and tryptophol derivatives via a Ag(I)-catalyzed enantioselective dearomative cyclization cascade sequence. The complex tetracyclic scaffolds are prepared via a rapid, versatile, three-step modular synthesis from simple commercially available indole derivatives in high yields and enantiomeric excess (up to 99% yield and >99% ee).
Topics & Concepts
ChemistryTryptamineEnantioselective synthesisYield (engineering)EnantiomerCascadeIndole alkaloidCombinatorial chemistryStereochemistryAlkaloidEnantiomeric excessIndole testStereoisomerismTotal synthesisOrganic chemistryCatalysisChromatographyMetallurgyMaterials scienceBiochemistryCatalytic C–H Functionalization MethodsAlkaloids: synthesis and pharmacologyChemical synthesis and alkaloids