engleski

Synthesis of phthalimide derivatives of adamantylamino acids

Adamantane is a very important pharmacophore that has been found in different classes of biologically active compounds.[1] Its derivatives activated by phthalimide chromophore can be photochemically transformed to more complex polycyclic molecules with potential biological activity.[2] We have recently reported the synthesis of 3-phthalimidoadamantane-1-carboxylic acid (1) and investigation of its photochemical reactivity in the reaction of photodecarboxylation.[3] In continuation of our research on the synthesis of unnatural adamantylamino acids and their photochemical reactivity, we have prepared a series of adamantylphthalimide derivatives 2-6. The molecules are designed to probe for the efficiency of photoinduced intramolecular electron transfer from the carboxylate to the phthalimide in the triplet excited state. Herein we report the synthesis and structural characterization of unnatural adamantane amino acids and their corresponding phthalimide derivatives 2-6.

phthalimide chromophore ; photodecarboxylation ; adamantylamino acids ; adamantylphthalimide derivatives

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