Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions

TY - JOUR

T1 - Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions

AU - Stephens, Thomas C

AU - Lawer, Aggie

AU - French, Thomas

AU - Unsworth, William Paul

N1 - © 2018 The Authors.

PY - 2018/9/18

Y1 - 2018/9/18

N2 - Macrocyclic lactones can be prepared from lactams and hydroxyacid derivatives via an efficient 3- or 4-atom iterative ring expansion protocol. The products can also be expanded using amino acid-based linear fragments, meaning that macrocycles with precise sequences of hydroxy- and amino acids can be assembled in high yields by 'growing' them from smaller rings, using a simple procedure in which high dilution is not required. The method should significantly expedite the practical synthesis of diverse nitrogen containing macrolide frameworks.

AB - Macrocyclic lactones can be prepared from lactams and hydroxyacid derivatives via an efficient 3- or 4-atom iterative ring expansion protocol. The products can also be expanded using amino acid-based linear fragments, meaning that macrocycles with precise sequences of hydroxy- and amino acids can be assembled in high yields by 'growing' them from smaller rings, using a simple procedure in which high dilution is not required. The method should significantly expedite the practical synthesis of diverse nitrogen containing macrolide frameworks.

KW - Journal Article

UR - http://www.scopus.com/inward/record.url?scp=85053029561&partnerID=8YFLogxK

U2 - 10.1002/chem.201803064

DO - 10.1002/chem.201803064

M3 - Article

C2 - 30011360

SN - 0947-6539

VL - 24

SP - 13947

EP - 13953

JO - Chemistry : A European Journal

JF - Chemistry : A European Journal

IS - 52

ER -