A new total synthesis of the two phenolic alkaloids (±)-cherylline 1 and (±)-latifine 2 isolated from Crinum species is described. The two key steps in the elaboration of these natural products are an anionic variant of the Fries rearrangement which gives access to the congested o-aroylbenzoic acid derivatives 26 and 27, and an intramolecular Horner reaction involving the corresponding N-phosphorylmethylbenzamide derivatives 8 and 9.
A. Couture, E. Deniau, S. Lebrun and P. Grandclaudon, J. Chem. Soc., Perkin Trans. 1, 1999, 789 DOI: 10.1039/A809925A
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