Site-Selective Synthetic Modifications of the Cinchona Alkaloids

Abstract

The natural product quinine has been known to humankind for centuries, and in that time has played a pivotal role in the treatment of malaria. Quinine, and the related cinchona alkaloids, have seen widespread contemporary use across chemical and biological disciplines, owing in part to the plethora of functional groups and stereochemical information contained within their scaffold. This review focuses on site-selective synthetic modifications of the cinchona alkaloids. Our comparative analysis may act as a ‘user manual’ for the selective functionalisation of the cinchona alkaloids, and aims to promote consideration of remarkable and lesser-understood aspects of cinchona chemistry.