The remarkable way that Nature prepares complex natural products has always been a source of inspiration to scientists, stimulating the development of new synthetic methods and strategies, as elegantly demonstrated by biomimetic approaches to total synthesis. Similarly, the performance and specificity of enzymes, perfected though evolution, offer ideals of selectivity and specificity that synthetic chemists aspire to. This proposal aims to develop an internationally leading research programme inspired by Nature’s ability to selectively generate diverse products from simple materials with exquisite levels of regio- and enantiocontrol. We aspire to synthetically emulate the elegant behaviour of Nature’s building blocks, such as co-enzyme A, in their ability to generate synthetic diversity (such as polyketides and alkaloids) from a simple and common starting material. Using this blueprint, we intend to selectively control the synthesis of a diverse range of bespoke stereodefined carbo- and heterocycles from readily available starting materials using simple man-made catalysts. We specifically aim to develop new strategies within the field of organic catalysis, focused upon the development of methods for the in situ catalytic generation of chiral ammonium enolates from carboxylic acids and their employment in catalysis. We also propose to develop a comprehensive mechanistic understanding of these processes. In preliminary work we have delineated a simple and efficient approach to this problem by employing chiral isothioureas as asymmetric catalysts, and we aim to build on the insight provided by these studies to develop this powerful concept into a generally applicable synthetic strategy.
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