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A Synthesis of (3S*,4R*)-Luffariolide
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1995
Year
Combinatorial ChemistryHeterocyclicAlkene MetathesisBiochemistryNatural SciencesHigher Order OrganocuprateOrganic ChemistryTrisubstituted AlkeneStereoselective SynthesisChemistry1,2-Metallate RearrangementHeterocycle ChemistryEnantioselective Synthesis
A 1,2-metallate rearrangement of a higher order organocuprate was a key step in the synthesis of a trisubstituted alkene in the marine sesterterpenoid Luffariolide E. The synthesis shows that the stereochemistry of Luffariolides C, D, and E is (3S,4R).