First highly stereocontrolled synthesis of the unusual 1-hydroxy endo,endo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignan skeleton

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• 作者：Ma&#xef ; wenn Jacolot^a ; Leyla Pehlivan^a ; Didier Bouyssi^a ; Nuno Monteiro^a ; Geneviè ; ve Balme ; ^a ; ^{balme@univ-lyon1.fr"" rel=""nofollow}
• 关键词：1-Hydroxy furofuran ; Epoxy esters ; Cyclization ; δ ; -Hydroxy-γ ; -butyrolactone
• 刊名：Tetrahedron Letters
• 出版年：2011
• 出版时间：14 September 2011
• 年：2011
• 卷：52
• 期：37
• 页码：4720-4723
• 全文大小：429 K

文摘

This Letter describes a highly diastereoselective synthesis of the unique 1-hydroxy endo,endo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane skeleton starting from a stereodefined 4-arylidenetetrahydrofuran obtained by a multicomponent reaction. The key step of this synthesis is a dealkylative cyclization reaction performed on the corresponding epoxide, generating four contiguous stereogenic centers with total stereocontrol.