What is it about?
Isobenzofuranones are known for their wide range of biological activities such as fungicide, insecticide, and anti-cancer. The search for novel bioactive compounds was performed by reaction of epoxide 2 with methanol, ethanol, propan-1-ol, propan-2-ol and butan-1-ol. The mechanism for the stereoselective and stereospecific epoxide opening was proposed based on theoretical calculations of the transition states. The compound (rac) -3a is the kinetic product as inferred from the lower energies of its transition state (TS1). The structures of the products were determined by NMR interpretation and theoretical calculations.
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Why is it important?
Isobenzofuranones or phthalides are a class of heterocyclic compounds commonly found in the plant, fungi, and bacteria kingdom. Heterocyclic compounds, such as these, have a broad spectra of bioactivities. The challenging task of establishing the relative stereochemistry of the isobenzofuranones was accomplished by NMR analyses, and theoretical calculations of the NMR chemical shifts. The mechanism of the reaction was proposed by calculating the transition states, confirming the structures proposed.
Perspectives
Structure determination was accomplished using three approaches: NMR analyses, theoretical calculations (MAE and DP4), and mechanism proposal. Diels-Alder reaction was the main step in the formation of the isobenzofuranones. All these topics are frequently found in the literature due to their importance.
Professor Elson Santiago Alvarenga
Universidade Federal de Vicosa
Read the Original
This page is a summary of: Computation and structural elucidation of compounds formed via epoxide alcoholysis, Magnetic Resonance in Chemistry, January 2019, Wiley,
DOI: 10.1002/mrc.4818.
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