Published in
Elsevier, Tetrahedron Letters, 37(52), p. 4720-4723
DOI: 10.1016/j.tetlet.2011.07.014
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First highly stereocontrolled synthesis of the unusual 1-hydroxy endo,endo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignan skeleton
Journal article published in 2011 by
Maïwenn Jacolot 
,
Leyla Pehlivan,
Didier Bouyssi,
Nuno Monteiro,
Geneviève Balme
,
Leyla Pehlivan,
Didier Bouyssi,
Nuno Monteiro,
Geneviève Balme
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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.