A short synthesis of (+/-)-epiasarinin.
[reaction: see text] Epiasarinin, an endo-endo furofuran, has been synthesized from piperonal via a five-step route with good stereocontrol. The sequence involves Darzens condensation, alkenyl epoxide-dihydrofuran rearrangement, and a Lewis acid mediated cyclization.
Aldous
David J
DJ
Department of Chemistry, University of Durham, South Road, Durham, DH1 3LE, UK.
Dalençon
Anne J
AJ
Steel
Patrick G
PG
D005663:Furans / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy
D005663:Furans; D007202:Indicators and Reagents; C454643:epiasarinin