We use cookies to ensure that we give you the best experience on our website. By continuing to browse this repository, you give consent for essential cookies to be used. You can read more about our Privacy and Cookie Policy.

Durham Research Online
You are in:

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.

Item Type:Article
Full text:Full text not available from this repository.
Publisher Web site:
Record Created:09 Jan 2008
Last Modified:08 Apr 2009 16:36

Social bookmarking: del.icio.usConnoteaBibSonomyCiteULikeFacebookTwitterExport: EndNote, Zotero | BibTex
Look up in GoogleScholar | Find in a UK Library