A cascade cyclization route to adjacent bistetrahydrofurans from chiral triepoxyfarnesyl bromides.
A number of isomeric bistetrahydrofuran analogues were prepared from triepoxy farnesyl bromides by a zinc-initiated reduction-elimination and in situ Lewis acid-promoted cascade cyclization.
Marshall
James A
JA
Department of Chemistry, University of Virginia, P.O. Box 400319, McCormick Road, Charlottesville, Virginia 22904, USA. jam5x@virginia.edu
Hann
Ronald K
RK
D002384:Catalysis; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D008956:Models, Chemical; D010084:Oxidation-Reduction; D054876:Prenylation; D013057:Spectrum Analysis; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D004852:Epoxy Compounds; D005663:Furans; D006842:Hydrocarbons, Brominated; C018674:tetrahydrofuran; D015032:Zinc