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Ring-Closing Alkyne Metathesis: Application to the Stereoselective Total Synthesis of Prostaglandin E2-1,15-Lactone
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2000
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Bioorganic ChemistryOrganic ChemistryChemistryDiyne MetathesisMedicinal ChemistryProstaglandin E2-1,15-lactoneStereoselective FormationStereoselective SynthesisBiochemistryPharmacologyNatural Product SynthesisAsymmetric CatalysisEnantioselective SynthesisRing-closing Alkyne MetathesisHeterocyclicAlkene MetathesisProstaglandin E2-1,5-lactoneStereoselective Total SynthesisNatural SciencesSynthetic Chemistry
The first total synthesis of a biologically relevant natural product (prostaglandin E2-1,5-lactone; see picture) by ring-closing diyne metathesis followed by Lindlar reduction is reported. This conceptually novel strategy allows the stereoselective formation of macrocyclic Z alkenes which cannot be accessed stereoselectively by conventional ring-closing olefin metathesis.