Enantioselective [4 + 2] Cycloaddition/Cyclization Cascade Reaction and Total Synthesis of <i>cis</i>-Bis(cyclotryptamine) Alkaloids
Jian Xu, Runze Li, Nian Xu, Xiaohua Liu, Fei Wang, Xiaoming Feng
Abstract
The asymmetric catalytic synthesis of 3-cyclotryptamine substituted oxindoles through formal [4 + 2] cycloaddition/cyclization cascade is described. A wide range of cyclotryptamine derivatives were obtained in enantioenriched form under mild reaction conditions and were found to have potential anticancer activity. The strategy enables ready assembly of cyclotryptamine subunits at the C3a–C3a′ positions with two quaternary stereogenic centers in cis-selectivity, leading to the concise synthesis of optically active cis-bis(hexahydropyrroloindole) and others of the cyclotryptamine alkaloid family.
Topics & Concepts
ChemistryEnantioselective synthesisCycloadditionCascadeTotal synthesisStereochemistryCascade reactionCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisChromatographyChemical synthesis and alkaloidsAsymmetric Synthesis and CatalysisAdvanced Synthetic Organic Chemistry