The Journal of Organic Chemistry · 2020 · 38 citations · 50 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryAlkaloid BiosynthesisCarbonyl ChemistryCatalytic MechanismsHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisAldol AdditionAldol CondensationAldol ReactionC-h ActivationIndole AlkaloidsIndole ChemistryIndole DerivativesPlant Alkaloids
A weakly coordinating carbonyl-directed coupling of allyl alcohols at the C-4 position of indole derivatives under the C-H activation conditions catalyzed by Rh(III) is reported. This results in alkylation at the C-4 position of indole derivatives exclusively. The obtained product forms a tricyclic derivative under aldol reaction conditions, which can be a potential precursor for synthesizing a few alkaloid molecules such as ergot, hapalindole alkaloids, and related heterocyclic compounds.
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Indole synthesis – something old, something new
Martyn Inman, Christopher J. Moody · Chemical Science · 2012 · 646 citations