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Synthetic and Cycloaromatization Studies on a Calicheamicin Model: An Example of Internal Quenching of the 1,4-Diyl Intermediate
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1993
Year
Inorganic Chemistry1,4-Diyl IntermediateDeuterium Labelling ExperimentsEngineeringHeterocyclicBiochemistryCalicheamicin ModelNatural Sciences3-Oms-1,5-hexadiyne UnitOrganic ChemistryInternal QuenchingChemistryHeterocycle ChemistryEnediyne BridgeChemical DerivativeSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
A precursor to the calicheamicin bicyclic core structure in which the enediyne bridge has been replaced by a 3-OMs-1,5-hexadiyne unit was synthesized with the purpose of investigating its ability to undergo cycloaromatization under basic conditions. Products arising from internal 1,5-hydrogen atom transfer were obtained which was confirmed by deuterium labelling experiments.