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A Pauson-Khand and ring-expansion approach to the aquariane ring system
Paul D Thornton1, D Jean Burnell
1Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada B3H 4J3.
Abstract:
[Structure: see text] The carbocyclic ring system of the aquariolide diterpenes has been synthesized by two routes involving a diastereoselective Pauson-Khand reaction and subsequent ring expansion. In one route, a tetracyclic enone was elaborated to generate the nine-membered ring by Grob fragmentation. In the second approach, a spirocyclic tricycle underwent a facile anionic oxy-Cope rearrangement to complete the synthesis of the desired ring system.
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