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The Synthesis of Structurally Diverse Macrocycles By Successive Ring Expansion. 2015
Christiana Kitsiou, and
Jordan J Hindes, and
Phillip I'Anson, and
Paula Jackson, and
Thomas C Wilson, and
Eleanor K Daly, and
Hannah R Felstead, and
Peter Hearnshaw, and
William P Unsworth
University of York, York, YO24 4PP (UK).
Structurally diverse macrocycles and medium-sized rings (9-24 membered scaffolds, 22 examples) can be generated through a telescoped acylation/ring-expansion sequence, leading to the insertion of linear fragments into cyclic β-ketoesters without performing a discrete macrocyclization step. The key β-ketoester motif is regenerated in the ring-expanded product, meaning that the same sequence of steps can then be repeated (in theory indefinitely) with other linear fragments, allowing macrocycles with precise substitution patterns to be "grown" from smaller rings using the successive ring-expansion (SuRE) method.
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