1384881-44-0Relevant articles and documents
Stereoselective functionalization of pyrrolidinone moiety towards the synthesis of salinosporamide A
Barbion, Julien,Sorin, Geoffroy,Selkti, Mohamed,Kellenberger, Esther,Baati, Rachid,Santoro, Stefano,Himo, Fahmi,Pancrazi, Ange,Lannou, Marie-Isabelle,Ardisson, Janick
, p. 6504 - 6512 (2012/08/27)
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.