Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 52, Pages 15794-15798Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201509153
Keywords
macrocycles; medium-sized rings; rearrangement; ring expansion; structural diversity
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- University of York
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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 beta-ketoesters without performing a discrete macrocyclization step. The key beta-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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