Giang Thanh Tran / Chemistry & Biochemistry / Faculty Mentor: Carl Lovely
The preparation of the key ketone from Fiedel-Craft acylation from 4-(1,3-dioxoisoindolin-2-yl)butanoic acid and 1,4-dimethoxybenzene resulted in the formation of 1-(2,5-dimethoxybenzoyl)-2,3-dihydro-5H-pyrrolo[2,1-a]isoindol-5-one as a major byproduct. The reaction was repeated under different temperature and duration conditions to optimize for the highest yield of the byproduct as it was perceived to be an interesting material for further elaboration. The reactivities of the functional groups of the molecule are also determined by performing various reactions, including Schmidt rearrangement, Beckmann rearrangement, Baeyer-Villager oxidation, Luche reduction, and hydrogenation. This exploration will set the stage for applications in the total synthesis of natural products in the “izidine” families.
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