Computational modeling is used to explore the energy barriers to the formation of cis- and trans-whiskey lactone from the glycoside of the corresponding open chain cis hydroxyacids. Two mechanisms are probed: a conventional nucleophilic attack by the hydroxyl on the protonated carbonyl group, and an attack of the acid group on an activated glycosidic bond. The former pathway proceeds with retention while the latter inverts the stereochemistry and provides a mechanism for potential interconversion of these isomers, an area of historical interest.

Possible explanation for the formation of trans-Whiskey lactone: A computational approach

249th National Meeting (2015)

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