Tandem metathesis reactions of oxabicyclo[2.2.1]heptenes: studies on the spirocyclic core of cyclopamine.

E Zachary Oblak, Narendran G-Dayanandan, Dennis L Wright

Department of Pharmaceutical Sciences, University of Connecticut, Storrs, Connecticut 06269, United States.

Organic letters 2011 May 6

filter terms:

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.

Citation

E Zachary Oblak, Narendran G-Dayanandan, Dennis L Wright. Tandem metathesis reactions of oxabicyclo[2.2.1]heptenes: studies on the spirocyclic core of cyclopamine. Organic letters. 2011 May 6;13(9):2433-5