Agelastatin A is a member of the oroidin-alkaloid family isolated from the marine sponge Agelas dendromorpha in 1993. It has shown potential for the treatment of cancer and Alzheimer's disease along with potent insecticidal activity; however, molecular-level details of the mechanism of action of this natural product are lacking including possible cellular receptors.  Building on our experience with the reactivity of imidazolones, a plausible biogenetic approach has been developed for the total synthesis of agelastatin A that involves an acyliminium cascade to construct the core rings of this target in a single step from a linear precursor.  Progress towards the construction of the key carbinolamide cyclization substrate will be detailed along with reactivity studies of a key alkyne-aldehyde and alkyne-acetal precursor by 1H NMR.

"Bio-inspired" strategy toward the total synthesis of agelastatin A

239th National Meeting (2010)

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