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Durham University

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Publication details for Prof. Patrick G. Steel

D.J. Aldous, A.S. Batsanov, D.S. Yufit, A.J. Dalencon, W.M. Dutton & P.G. Steel (2006). The dihydrofuran template approach to furofuran synthesis. Organic & Biomolecular Chemistry 4(15): 2912-2927.

Author(s) from Durham


Flash vacuum pyrrolysis of vinyl epoxides provides cis-dihydrofuran carboxylic esters in good yields and diastereoselectivities, which, on base-promoted epimerisation afford the complementary trans series. The compounds provide a viable template for a Lewis acid promoted cyclisation to provide the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane core found in the furofuran series of natural lignans. This strategy is stereodivergent and can be controlled to provide the exo-exo, exo-endo or endo-endo stereochemistries. The approach has been exemplified in syntheses of the sesamyl furofurans (±)-epiasarinin and (±)-asarinin.