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Total Synthesis of (−)-Mucocin
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1999
Year
Diversity Oriented SynthesisAnnonaceous AcetogeninBioorganic ChemistryEngineeringBiochemistryNatural SciencesDiversity-oriented SynthesisTotal SynthesisOrganic ChemistryChemistryModular StrategyPharmacologySynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringNatural Product Synthesis
A highly convergent, modular strategy for the total synthesis of the annonaceous acetogenin (−)-mucocin is reported. The remarkable features are the endo-selective formation of the tetrahydropyran ring from an activated epoxide and the stability of the butenolide in the coupling with an organomagnesium compound.