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Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions.

ABSTRACT: 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.

SUBMITTER: Stephens TC

PROVIDER: S-EPMC6334170 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions.

Stephens Thomas C TC Lawer Aggie A French Thomas T Unsworth William P WP

Chemistry (Weinheim an der Bergstrasse, Germany) 20180819 52

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 div ...[more]

PMID: 30011360

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