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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.


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

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PMID: 21456515

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