Modern Macrolactonization Techniques

Max Van Hoof; Guillaume Force; David Lebœuf

doi:10.1055/a-2181-9800

Synthesis, Table of Contents

Synthesis 2024; 56(05): 714-732
DOI: 10.1055/a-2181-9800

short review

Modern Macrolactonization Techniques

Max Van Hoof

^aInstitut de Science et d’Ingénierie Supramoléculaires (ISIS), CNRS UMR7006, Université de Strasbourg, 67000 Strasbourg, France

,

Guillaume Force

^bInstitut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), CNRS UMR 8182, Université Paris-Saclay, 91405 Orsay, France

,

David Lebœuf ∗

^aInstitut de Science et d’Ingénierie Supramoléculaires (ISIS), CNRS UMR7006, Université de Strasbourg, 67000 Strasbourg, France

› Author Affiliations

Abstract

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Abstract

The study of macrolactonization processes has been a steady endeavor for synthetic chemists to access macrocycles that are fundamental in the development of numerous high-added-value compounds, notably drugs and fragrances. This field of research is essential as macrolactonizations usually take place at the end of manifold syntheses and chemists need reliable, efficient, and versatile tools to avoid unpredictable results that would lead them to completely redesign their synthetic plan. Here, we highlight the recent methods reported to achieve macrolactonizations towards the formation of both macrolactones and macrodiolides, which feature either Lewis acids, transition metals or organic molecules as activating agents.

1 Introduction

2 Stoichiometric Carboxylic Acid Activation

3 Lewis Acid Catalyzed Reaction

4 C–H Activation

5 Ring-Expansion Strategy

6 Chemoenzymatic Synthesis

7 Other Macrolactonization Variants

8 Conclusion and Outlook

Key words

macrolactone - macrodiolide - coupling agent - Lewis acid - C–H activation - ring expansion - chemoenzymatic

Full Text

References

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