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Synlett 1992; 1992(6): 479-480
DOI: 10.1055/s-1992-21383
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Alternative Approach to 2,6-Diaryl-3,7-dioxabicyclo [3.3.0]octane Lignans Using an Alicyclic Claisen Rearrangement

Hilary M. Bradley* , Richard G. Jones, David W. Knight
  • *Chemistry Department, University Park, Nottingham NG7 2RD, England
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Publication Date:
08 March 2002 (online)

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A stereoselective approach to 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans 4 has been developed in which the key step is a stereospecific enolate Claisen rearrangement of the macrolide 13 (6-aryl-2-oxo-3,4,6,9-tetrahydro-2H-1,5-dioxonin) leading to the pivotal intermediate, methyl 5-aryl-4-vinyltetrahydrofuran-3-carboxylate 14a.