Acid-promoted Cyclization of Tetronic Acid to Alkene; Chemical Transformation of (-)-Ircinianin to (+)-Wistarin.

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  • Acid-promoted Cyclization of Tetronic A

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Abstract

The perchloric acid-promoted transformation of (-)-ircinianin (1) to (+)-wistarin (2) is described. The reaction of 1 with perchloric acid in acetonitrile gave 2 in 35% yield along with a positional isomer 4 in 35% yield. The structure of 4 was determined by two dimensional (2D) NMR studies. On the other hand, the reaction of 2-methyl-4-prenyltetronic acid (6), as a model compound for the above transformation, gave the cyclized product 8 corresponding to 2 in 58% yield and the keto-lactone 9 in 22% yield under the same conditions.

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