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.

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
• Public URL: https://durham-repository.worktribe.com/output/1565372