A new family of imidazole alkaloids isolated from the Fijian Calcareous sponge Leucetta sp. spirocalcaridine A and spirocalcaridine B, have attracted attention for their structural uniqueness. The core framework contains a distinctive hexahydrocyclopentamidazol-2-ylidenamine spiro-linked to a cyclohexadienone ring although the relative and absolute stereochemistry are unknown.  Previous attempts to synthesize these two molecules in our lab were based on ipso-cyclization of aryl ynenone followed by synthesis of imidazole ring. The current approach consists of synthesis of a propargylguanidine followed by a tandem formation of imidazole and spiro ring under oxidative condition

Studies toward the total synthesis of 2-aminoimidazole alkaloids

247th National Meeting (2014)

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