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The dihydrofuran template approach to furofuran synthesis.

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


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.

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Date of first online publication:August 2006
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