Angewandte Chemie International Edition · 2015 · 103 citations · 53 references
Natural SciencesChemistryMedicinal ChemistryCatalysisNatural Product BiosynthesisOrganic ChemistryHeterocycle SynthesisOrganic SynthesisRetrosynthetic AnalysisSteroid BiosynthesisTerpenoid BiosynthesisAldehydesCobalt-catalyzed Cross-couplingDiterpene BiosynthesisEnantioselective SynthesisHeterocyclic Natural ProductsNatural Product SynthesisNatural Product Total SynthesisRing-forming Reactions
Two enantioselective total syntheses of the nortriterpenoid natural product rubriflordilactone A are described, which use palladium- or cobalt-catalyzed cyclizations to form the CDE rings, and converge on a late-stage synthetic intermediate. These key processes are set up through the convergent coupling of a common diyne component with appropriate AB-ring aldehydes, a strategy that sets the stage for the synthetic exploration of other members of this family of natural products.
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A stereoselective synthesis of (Z)-1-iodo-1-alkenes
Gilbert Stork, Kang Zhao · Tetrahedron Letters · 1989 · 364 citations