The synthesis of structurally diverse macrocycles by successive ring expansion

TY - JOUR

T1 - The synthesis of structurally diverse macrocycles by successive ring expansion

AU - Unsworth, William Paul

AU - Kitsiou, Christiana

PY - 2015

Y1 - 2015

N2 - Structurally diverse macrocycles and medium sized rings (9–24 membered scaffolds, 22 examples) can be generated via a telescoped acylation/ring expansion sequence, leading to the insertion of linear fragments into cyclic β-ketoesters without performing a discrete macrocyclisation 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.

AB - Structurally diverse macrocycles and medium sized rings (9–24 membered scaffolds, 22 examples) can be generated via a telescoped acylation/ring expansion sequence, leading to the insertion of linear fragments into cyclic β-ketoesters without performing a discrete macrocyclisation 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.

KW - Macrocycles • Medium-sized Rings • Ring Expansion • Rearrangements • Diversity

U2 - 10.1002/anie.201509153

DO - 10.1002/anie.201509153

M3 - Article

SN - 1433-7851

VL - 54

SP - 15794

EP - 15798

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 52

ER -