Organic Letters · 2007 · 45 citations · 13 references
PharmacyChemistryMedicinal ChemistryOrganic ChemistryStructure-activity RelationshipsSynthetic Medicinal ChemistryDiversity-oriented SynthesisHeterocycle SynthesisMacrocycle SynthesisOrganic SynthesisRetrosynthetic AnalysisAsymmetric Heterocycle SynthesisBicyclononyne ChemistryConformational BiasEnyne CyclizationMacrocycle DiversificationMacrocyclic Library ConstructionRing-forming ReactionsSynthetic Route Optimization
[reaction: see text] An efficient synthetic route to the ABC tricyclic core of 1alpha-alkyldaphnanes has been developed. The conformational bias imparted by the C6-C9 oxo-bridge of BC-ring system 12 was used to elaborate the ABC-ring system precursor including the introduction of the beta-C5 hydroxyl group. A completely diastereoselective palladium-catalyzed enyne cyclization was then employed to establish the A-ring with a C1 appendage.
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