A Pauson-Khand and ring-expansion approach to the aquariane ring system.
[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.
Thornton
Paul D
PD
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada B3H 4J3.
Burnell
D Jean
DJ
D000818:Animals; D037421:Anthozoa / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D004224:Diterpenes