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The Synthesis of Structurally Diverse Macrocycles By Successive Ring Expansion
Author(s) -
Kitsiou Christiana,
Hindes Jordan J.,
I'Anson Phillip,
Jackson Paula,
Wilson Thomas C.,
Daly Eleanor K.,
Felstead Hannah R.,
Hearnshaw Peter,
Unsworth William P.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201509153
Subject(s) - ring (chemistry) , sequence (biology) , chemistry , acylation , structural motif , stereochemistry , organic chemistry , catalysis , biochemistry
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.