Organic Letters · 2004 · 75 citations · 11 references
Natural SciencesChemistryMedicinal ChemistryNatural Product BiosynthesisOrganic ChemistrySynthetic Medicinal ChemistryCross-coupling ReactionsHeterocycle SynthesisHeterocyclic ChemistryMacrocycle SynthesisOrganic SynthesisRetrosynthetic AnalysisAsymmetric SynthesisChiral Product SynthesisEnantioselective SynthesisFuran SynthesisNatural Product Total SynthesisRing-closing MetathesisRing-forming ReactionsTotal Synthesis-derived Analogues
A strategy for the synthesis of chiral 5-(1-hydroxyalk-2-enyl)-5H-furan-2-ones and its application to the total synthesis of (-)-muricatacin, in four steps and 37% overall yield from (R,R)-hexa-1,5-diene-3,4-diol, are described. The key synthetic step in this approach is a highly regioselective and stereoselective tandem ring-closing/cross metathesis reaction in which both lactone formation and alkyl chain extension are accomplished in an efficient one-pot process.
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