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A Synthesis of (3R*,4R*)-Luffariolide E via 1,2-Metallate Rearrangement
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1995
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Key StepBioorganic ChemistryEngineeringOrganic ChemistryChemistryHeterocycle ChemistryDiversity Oriented SynthesisStereoselective SynthesisSynthetic ProductCross-coupling ReactionDiversity-oriented SynthesisHigher Order CupratePharmacologyNatural Product SynthesisEnantioselective SynthesisBiomolecular EngineeringAlkene MetathesisNatural Sciences1,2-Metallate Rearrangement
A key step in the synthesis of (3R*,4R*)-Luffariolide E is a 1,2-metallate rearrangement of a higher order cuprate to generate a trisubstituted double bond stereoselectively. The synthetic product is a diastereoisomer of the natural marine cytotoxic agent (3S,4R)-Luffariolide E.