Synthetic Studies on Spirolide, a Macrocyclic Alkaloid, having potential neurotoxicity

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Spirolide is a marine natural product, having strong neurotoxicity. The structure was featured by the macrocyclic framework containing the azaspirocyclic moiety and the bisspiroacetal. The absolute configuration at C-2 and C-4 has not been clarified, and the precise mode of action still remains unknown. We have studied the synthesis of this natural toxin to clarify the complete structure. The framework of the upper half fragment, having cyclohexene ring, was constructed by chiral templated Diels-Alder reaction and the lower half fragment, having spirocyclic system, was successfully synthesized.