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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|Publisher Web site:||http://dx.doi.org/10.1039/b604952d|
|Record Created:||09 Jan 2008|
|Last Modified:||08 Apr 2009 16:36|
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