Organic Letters · 2009 · 22 citations · 25 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryCross-coupling ReactionsHeterocycle SynthesisMacrocycle SynthesisOrganic SynthesisCross-coupling CatalysisOxidative CouplingOxidative Coupling ReactionsOxidative Cross-couplingPalladium-catalyzed Cross-couplingStereoselective Cross-couplingSuzuki - Miyaura CouplingTransition-metal-catalyzed Cross-coupling
Carpanone has been stereoselectively synthesized in 55% yield and six steps from sesamol. The key step of the synthetic sequence is the direct introduction of the propenyl side chain via a Suzuki-Miyaura cross-coupling reaction. The subsequent Pd(II)-catalyzed oxidative coupling yields carpanone as a single diastereoisomer independently of the geometric configuration of the starting precursor. A new mechanism is proposed for this transformation.
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