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A New Cross-Coupling-Based Synthesis of Carpanone

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journal contribution
posted on 01.10.2009, 00:00 by Frédéric Liron, Francesco Fontana, Jean-Olivier Zirimwabagabo, Guillaume Prestat, Jamshid Rajabi, Concetta La Rosa, Giovanni Poli
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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