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The dihydrofuran template approach to furofuran synthesis

Aldous, D.J.; Batsanov, A.S.; Yufit, D.S.; Dalencon, A.J.; Dutton, W.M.; Steel, P.G.

Authors

D.J. Aldous

D.S. Yufit

A.J. Dalencon

W.M. Dutton



Abstract

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.

Citation

Aldous, D., Batsanov, A., Yufit, D., Dalencon, A., Dutton, W., & Steel, P. (2006). The dihydrofuran template approach to furofuran synthesis. Organic and Biomolecular Chemistry, 4(15), 2912-2927. https://doi.org/10.1039/b604952d

Journal Article Type Article
Publication Date Aug 1, 2006
Deposit Date Jan 9, 2008
Journal Organic and Biomolecular Chemistry
Print ISSN 1477-0520
Electronic ISSN 1477-0539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 4
Issue 15
Pages 2912-2927
DOI https://doi.org/10.1039/b604952d


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