The Synthesis of Structurally Diverse Macrocycles By Successive Ring Expansion

Angewandte Chemie
Christiana KitsiouWilliam P Unsworth

Abstract

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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Citations

Mar 16, 2017·Chemistry : a European Journal·James R Donald, William P Unsworth
Mar 13, 2018·Biopolymers·Diana P SloughYu-Shan Lin
Sep 6, 2017·Organic & Biomolecular Chemistry·James A Rossi-AshtonWilliam P Unsworth
Aug 5, 2017·Chemistry : a European Journal·Rodrigo Mendoza-SanchezAndrei K Yudin
Jul 17, 2018·Chemistry : a European Journal·Thomas C StephensWilliam P Unsworth
Sep 5, 2018·Angewandte Chemie·Na WangXin-Yuan Liu
Oct 10, 2019·Macromolecular Rapid Communications·Yang LiangZi-Long Li
Aug 23, 2019·Chemistry : a European Journal·Anna DierksJens Christoffers
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Dec 10, 2016·Chemistry : a European Journal·Laetitia G BaudWilliam P Unsworth
Jul 20, 2017·Chemistry : a European Journal·Thomas C StephensWilliam P Unsworth
Dec 9, 2020·Chemistry : a European Journal·Jing ShangCraig A Hutton
Jan 26, 2021·Organic & Biomolecular Chemistry·Kleopas Y PalateWilliam P Unsworth
Mar 2, 2020·Chemical Science·Aimee K Clarke, William P Unsworth
Jun 28, 2019·Chemical Reviews·Kim T MortensenDavid R Spring
Dec 9, 2017·Organic Letters·Toshimune NomuraTohru Fukuyama
Aug 14, 2018·The Journal of Organic Chemistry·Angelina OsipyanMikhail Krasavin

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