title: Tandem metathesis reactions of oxabicyclo[2.2.1]heptenes: studies on the spirocyclic core of cyclopamine.
abstract: A rapid approach to the spirocyclic core of cyclopamine was achieved in four steps from 2-pentenyl-furan. A furan Diels-Alder reaction followed by a one-pot dehalogenation/amination sequence provides the oxabicyclic triene that upon treatment with Grubbs' catalyst undergoes smooth rearrangement to the tricyclic core.
authors: Department of Pharmaceutical Sciences, University of Connecticut, Storrs, Connecticut 06269, United States.
authors: E Zachary
authors: EZ
authors: Oblak
authors: Narendran
authors: N
authors: G-Dayanandan
authors: Dennis L
authors: DL
authors: Wright
mesh_terms: D003500:Cyclization; D005663:Furans / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry*; D014704:Veratrum Alkaloids / Q000737:chemistry*
chemical_list: D005663:Furans; D006576:Heterocyclic Compounds, 4 or More Rings; D013141:Spiro Compounds; D014704:Veratrum Alkaloids; C039281:furan; C000541:cyclopamine