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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201509153
Subject(s) - ring (chemistry) , chemistry , organic chemistry
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.