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Synthesis of a 14β-Hydroxysteroid Using the Transannular Diels-Alder Strategy
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1997
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Cross-coupling ReactionTransannular Diels-alder StrategyEngineeringHeterocyclicBiochemistryExcellent YieldNatural Sciencesπ-Allylpalladium ComplexTetracyclic Compound 2Organic ChemistryStereoselective SynthesisChemistryHeterocycle ChemistryNatural Product SynthesisSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
Macrocyclic TCC triene 1, generated by an intramolecular alkylation of a β-ketoester on a π-allylpalladium complex followed by dehydrogenation, underwent a highly stereoselective transannular Diels-Alder reaction affording the tetracyclic compound 2 in an excellent yield.