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Diels-Alder Reaction of a 2-Vinyltryptamine: An Approach to the Echitamine Ring System
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1992
Year
Dimethyl MaleateEngineeringHeterocyclicAlkene MetathesisIndole Alkaloid EchitamineOrganic ChemistryEchitamine Ring SystemStereoselective SynthesisChemistryDiels-alder CyclizationHeterocycle ChemistryPharmacologySynthetic ChemistryBiomolecular EngineeringDiels-alder Reaction
Diels-Alder cyclization of N-benzyl-N′-methoxycarbonyl-2-vinyltryptamine (5) with dimethyl maleate yielded a tetracyclic compound 7 [9-benzyl-3,4,10-trimethoxycarbonyl-1,2,3,4-tetrahydro-9a, 4a-(iminoethano)-9H-carbazole] with structural features closely related with those of the indole alkaloid echitamine (4).