European Journal of Organic Chemistry · 2012 · 35 citations · 53 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryCatalytic MechanismsHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisIndole AlkaloidsIndole ChemistryIndole DerivativesIndole SynthesisIsoquinoline SynthesisQuinoline ChemistryQuinoline SynthesisStereoselectivity
Abstract We report an iodine‐catalyzed Povarov reaction using indole as dienophile carried out in toluene at room temperature. This three‐component reaction, coupling an aldehyde, an amine, and an indole, proved to be an efficient method for synthesizing exo ‐indolo[3,2‐ c ]quinoline derivatives related to the alkaloid isocryptolepine (cryptosanguinolentine) in good yield and with high stereoselectivity.
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New alkaloids from Cryptolepis sanguinolenta
K. Cimanga, Tess De Bruyne, Luc Pieters et al. · Tetrahedron Letters · 1996 · 189 citations