Biomimetically-guided total syntheses of the Leucetta-derived alkaloids, kealiinines A-C have been accomplished using an intramolecular Friedel-Crafts-dehydration sequence of a bis benzylic alcohol. The precursor diol was obtained through a series of position specific Grignard reactions from 1-methyl-4, 5-diiodoimidazole. Two additional alkaloids, kealiiquinone and 2-deoxy-2-aminokealiiquinone, were obtained from a late stage kealiinine C intermediate by oxidation.

Total syntheses of kealiinines A-C along with kealiiquinone and 2-deoxy-2-aminokealiiquinone

245th National Meeting (2013)

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