Use in Total Synthesis
Five-membered carbon rings are ubiquitous structural motifs in natural products. In contrast to the larger, fully "consonant" cyclohexane scaffold cyclopentanes and their derivatives are "dissonant" according to the Lapworth-Evans model of alternating polarities. The dissonance in polarity clearly limits the ways by which cyclopentanes can be disconnected which becomes evident in the decreased number of general methods available for making five-membered rings versus the corresponding six-membered rings. Especially the fact that there is no Diels-Alder-equivalent for the synthesis of five-membered rings has been bothering synthetic chemists for many decades. Consequentially, after the vinylcyclopropane rearrangement was discovered around 1960 it didn't take long for the synthetic community to realize the potential inherent to form cyclopentenes by means of the vinylcyclopropane rearrangement. As the vinylcyclopropane rearrangement progressed as a methodology and the reaction conditions improved during the 1970s, first total syntheses making use of the vinylcycopropane rearrangement started to appear around 1980. Key figures to apply this reaction in total synthesis were Barry M. Trost, Elias J. Corey, Thomas Hudlicky, Leo A. Paquette,
Read more about this topic: Vinylcyclopropane Rearrangement
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