期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 16, 页码 6931-6936出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo2010846
关键词
-
资金
- National Center of Research and Development [ZPB/51/64927/IT/10]
- ADAMED Ltd.
A formal synthesis of a powerful cholesterol inhibitor, ezetymibe 1, is described. The crucial step of the synthesis is based on Cu(I)-mediated Kinugasa cycloaddition/rearrangement cascade reaction between terminal acetylene derived from acetonide of L-glyceraldehyde and suitable C,N-diarylnitrone. The adduct with (3R,4S) configuration at the azetidinone ring, obtained with high stereoselectivity, was subsequently subjected to deprotection of the diol side chain followed by glycolic cleavage and base-induced isomerization at the C3 carbon atom to afford the (3S,4S) aldehyde, which has been already transformed into ezetimibe by the Schering-Plough group.
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