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.
A new cross-coupling based synthesis of Carpanone / F. Liron, F. Fontana, J.O. Zirimwabagabo, G. Prestt, J. Rajabi, C. La Rosa, G. Poli. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 11:19(2009), pp. 4378-4381.
A new cross-coupling based synthesis of Carpanone
F. FontanaSecondo
;C. La RosaPenultimo
;
2009
Abstract
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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