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Structure Determination and Mechanism of Formation of a seco-Moreliane Derivative Supported by Computational Analysis.

Pablo A Chacón Morales, Juan M Amaro-Luis, Andrei G Kutateladze
Journal of Natural Products 2017 April 29
Basic hydrolysis of a dichloromethane extract of Stevia lucida yielded (4R,5S,7R,9R,10R,11R)-7,9-dihydroxylongipin-2-en-1-one (1), which was oxidized and subjected to acidic conditions to generate the new seco-moreliane derivative 3. The structure of 3 was established based on NMR data interpretation and confirmed computationally. A plausible mechanism for the carbocationic rearrangement of the trione 2 to the seco-moreliane 3 was supported by DFT computations.

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