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The Baker-Venkataraman Rearrangement

In the world of organic synthesis, constructing complex heterocyclic rings often requires elegant rearrangement reactions. Among the most useful for medicinal chemists and natural product researchers is the Baker-Venkataraman Rearrangement . This reaction is not just a textbook curiosity; it is a fundamental gateway to synthesizing flavones and chromones , structures found abundantly in nature with significant biological activities. What is the Baker-Venkataraman Rearrangement? At its core, the Baker-Venkataraman rearrangement is a base-catalyzed transformation of 2'-acetoxyacetophenones (or generally, o-acyloxyketones) into 1,3-diketones (specifically, o-hydroxydibenzoylmethanes). It is essentially an intramolecular Claisen condensation . While a standard Claisen condensation involves two separate ester molecules, this rearrangement happens within a single molecule, driven by the proximity of the reacting groups. The General Reaction Scheme The starting material is usually prepa...