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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| Authors: | Maï wenn JacolotLeyla Pehlivan,Didier BouyssiNuno Monteiro,Geneviè ve Balme |
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| Affiliation: | ICBMS, Institut de Chimie et de Biochimie Moléculaires et Supramoléculaires (UMR 5246 du CNRS), Université Lyon 1-ESCPE Lyon, 43 Bd du 11 novembre 1918, 69622 Villeurbanne, France |
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| Abstract: | ![]()
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. |
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| Keywords: | 1-Hydroxy furofuran Epoxy esters Cyclization δ-Hydroxy-γ-butyrolactone |
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