Recent Advances in the Synthesis of Sesquiterpenolides from Umbelliferae

Within the context of Molecular Electronic Density Theory (MEDT), this study investigates the Diels–Alder reaction among isoprene (2) and R-carvone (1R) applying DFT simulations, with and without Lewis acid (LA) catalysis. The results show that carvone (1R) acts as an electrophile and isoprene (2) as a nucleophile in a polar process. LA catalysis increases the electrophilicity of carvone, thereby improving the reactivity and selectivity of the reaction by reducing the activation Gibbs free energy. Parr functions reveal that the C5=C6 double bond is more reactive than the C9=C10 double bond, indicating chemoselectivity. The examination of the Electron Localization Function (ELF) reveals high regio- and stereoselectivity, indicating an asynchronous mechanism for the LA-catalyzed DA reaction. Furthermore, it is suggested that cycloadduct 3 has great anti-HIV potential because it exhibits lower binding energies than azidothymidine (AZT) in the docking studies of cycloadducts 3 and 4 amongst a primary HIV-1protein (1A8O plus 5W4Q).

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Recent Advances in the Synthesis of Sesquiterpenolides from Umbelliferae

Abstract: A review of our latest developments in the synthesis of sesquiterpenolides isolated from plants of the Umbelliferae family is presented.

Cited by 2 publications

References 46 publications

ChemInform Abstract: Recent Advances in the Synthesis of Sesquiterpenolides from Umbelliferae

ChemInform Abstract: Recent Advances in the Synthesis of Sesquiterpenolides from Umbelliferae

MEDT analysis of mechanism and selectivities in non-catalyzed and lewis acid-catalyzed diels–alder reactions between R-carvone and isoprene

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