Synthesis of 2,5-disubstituted tetrahydrofurans by stereospecific elimination-cyclization of 1-iodomethyl-1,5-bis-epoxides.
[reaction: see text] Treatment of 1-iodomethyl-1,5-bis-epoxides with zinc in refluxing ethanol affords cis or trans 2-vinyl-5-(1-hydroxyethy)-substituted tetrahydrofurans stereospecifically in high yield.
Marshall
James A
JA
Department of Chemistry, University of Virginia, P.O. Box 400319, Charlottesville, Virginia 22904, USA. jam5x@virginia.edu
Chobanian
Harry R
HR
D000818:Animals; D037421:Anthozoa / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy
C476915:1-iodomethyl-1,5-bis-epoxide; D004852:Epoxy Compounds; D005663:Furans; D007202:Indicators and Reagents