A Domino Dearomative <i>ipso</i>-Annulation/Desymmetrization Approach: Stereoselective Access to Tricyclic Alkaloid Skeletons
Chada Raji Reddy, A. Prasad, Uprety Ajaykumar
Abstract
Herein, we reveal an unprecedented domino annulation of N -benzyl-acrylamides with 1,3-dicarbonyls for the assembly of fused tricyclic alkaloid frameworks incorporating a spirocycle via an alkylation/dearomative ipso -annulation/Michael addition (desymmetrization) sequence. This conversion involves three carbon–carbon bond formations, generating four chiral carbons, including three quaternary carbon centers, in a single diastereomer in one pot under identical reaction conditions. The synthetic potential of this atom-economic method is illustrated by modifications of the functional groups present in the products obtained.
Topics & Concepts
AnnulationDesymmetrizationDominoChemistryTricyclicStereoselectivityStereochemistryAlkaloidCombinatorial chemistryOrganic chemistryEnantioselective synthesisCatalysisAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsAdvanced Synthetic Organic Chemistry