From Discovery to Application: 50 Years of the Vinylcyclopropane–Cyclopentene Rearrangement and Its Impact on the Synthesis of Natural Products

A classic that hasn't lost its charm: The historical origins and current status of the vinylcyclopropane–cyclopentene rearrangement and the corresponding transformations of heteroatom-containing analogues (see scheme) are described in the context of methodology development and natural products synthesis. Several important events that greatly influenced the author's own research program some 30 to 40 years ago are recounted as personal recollections.