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  • Title: Synthesis of a functionalized 7,6-bicyclic spiroimine ring fragment of the spirolides.
    Author: Guéret SM, Furkert DP, Brimble MA.
    Journal: Org Lett; 2010 Nov 19; 12(22):5226-9. PubMed ID: 21028788.
    Abstract:
    The asymmetric synthesis of a functionalized 7,6-spiroimine related to the spirolides is described. Intermolecular Diels-Alder cycloaddition of a chiral trisubstituted dienophile and Danishefsky's diene enabled simultaneous installation of the C7 and C29 stereocenters. Further transformations and late-stage aza-Wittig cyclization afforded the spiroimine in good yield. During this study, an unprecedented 14-membered dialdimine was also obtained.
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