Facile synthesis of isocampholenic acids by the rearrangement of camphor derivatives

A variety of substituted isocampholenic acid derivatives were prepared by rearrangement of the camphor skeleton of a variety of tertiary alcohols derived from ketopinic acid. The reaction was highly reliable and retained the stereochemical information from the camphor scaffold. This rearrangement represents an efficient way to prepare synthetically useful isocampholenic acids. Mechanistic experiments show that a short-lived carbocation is implicated in the reaction.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide