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Article Dans Une Revue Tetrahedron Année : 2012

Stereoselective functionalization of pyrrolidinone moiety towards the synthesis of salinosporamide A

Résumé

An important feature of the synthesis of salinosporamide A, a potent proteasome inhibitor, is the establishment of the quaternary stereocenter at C3. A new route has been developed based on the methylation of a functionalized pyrrolidinone. Direct methylation reaction led to the unwanted diastereomer; however, by means of a Corey–Chaykovsky reaction followed by LiAlH4 epoxide opening, the desired alcohol was obtained. The pyrrolidinone was elaborated through a key allylation reaction between a tertiary allyltitanium reagent and an aldehyde bearing a spiroketal moiety in α-position
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Dates et versions

hal-02370605 , version 1 (14-10-2021)

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Julien Barbion, Geoffroy Sorin, Mohamed Selkti, Esther Kellenberger, Rachid Baati, et al.. Stereoselective functionalization of pyrrolidinone moiety towards the synthesis of salinosporamide A. Tetrahedron, 2012, 68 (32), pp.6504-6512. ⟨10.1016/j.tet.2012.05.103⟩. ⟨hal-02370605⟩
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