Stereoselective functionalization of pyrrolidinone moiety towards the synthesis of salinosporamide A |
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| Authors: | Julien Barbion Geoffroy Sorin Mohamed Selkti Esther Kellenberger Rachid Baati Stefano Santoro Fahmi Himo Ange Pancrazi Marie-Isabelle Lannou Janick Ardisson |
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| Affiliation: | 1. Faculté de Pharmacie, CNRS UMR 8638, Université Paris Descartes, 4 avenue de l''Observatoire, 75270 Paris Cedex, France;2. Faculté de Pharmacie, CNRS UMR 8015, Université Paris Descartes, 4 avenue de l''Observatoire, 75270 Paris Cedex, France;3. Faculté de Pharmacie, CNRS UMR 7200, Université de Strasbourg, 74 route du Rhin, 67400 Illkirch, France;4. Faculté de Pharmacie, Université de Strasbourg, CNRS-UMR 7199, Laboratoire des Systèmes Chimiques Fonctionnels, 74 route du Rhin, 67400 Illkirch, BP 60024, France;5. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden |
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| Abstract: | 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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