Total Synthesis of Iheyamine A via the Cyanide-Catalyzed Imino-Stetter Reaction
Jiye Jeon, Hyung Joo Kim, Cheol‐Hong Cheon
Abstract
The total synthesis of iheyamine A from readily available ethyl 2-aminocinnamate and 5-methoxyindole-2-carboxaldehyde is described. The cyanide-catalyzed imino-Stetter reaction of an aldimine derived from ethyl 2-aminocinnamate and 5-methoxyindole-2-carboxaldehyde provided the desired unsymmetrical 2,2'-bisindole-3-acetic acid derivative. The subsequent introduction of an amino group at the C-3' position, followed by the formation of the azepine ring, completed the total synthesis of iheyamine A.
Topics & Concepts
ChemistryAldimineAzepineCatalysisCyanideAcetic acidDerivative (finance)Ring (chemistry)Total synthesisStereochemistryOrganic chemistryMedicinal chemistryEconomicsFinancial economicsAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry MethodsAdvanced Synthetic Organic Chemistry