Synthesis 2021; 53(05): 785-804
DOI: 10.1055/s-0040-1705965
review

Recent Advances in One-Pot Enyne Metathesis Processes for the Preparation of Biologically and Medicinally Relevant Compounds

Eric Bernardi
,
Lino Colombo
,
Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 2700 Pavia, Italy   Email: massimo.serra@unipv.it
› Author Affiliations
Financial support from the Ministero dell’Istruzione, dell’Università e della Ricerca (MIUR) (Italian Ministry of Education, University and Research) is gratefully acknowledged (PRIN2015 prot. 20157WW5EH).


Abstract

Enyne metathesis reactions are powerful tools for the preparation of a wide range of synthetic and natural chemical substances with increasing efficiency and environmental sustainability. The driving force of the reaction is the formation of a stable conjugated system, i.e., a diene, which through further functionalization steps can be used for the construction of skeletally complex molecular architectures. These concepts are exploited to design cascade reaction sequences, where multiple rings can be formed in a one-pot fashion by combining metathetic protocols with various chemical transformations. The strong correlation between synthetic organic chemistry and medicinal chemistry prompted us to review the most notable approaches for the synthesis of biologically relevant compounds via enyne metathesis-based one-pot processes. With the aim to provide a modern and practical overview, by taking into consideration the scientific literature on this topic, we have focused the majority of our attention on the research performed in the last decade. This review covers the literature from 2003 to 2020.

1 Introduction

2 Ethylene-Mediated Processes

3 RCEYM/CM and CEYM/RCM Processes

4 Enyne Metathesis/Diels–Alder-Based Processes

5 RCM of Dienynes

6 RCM of Tethered Dienynes

7 Relay Metathesis

8 Ring-Rearrangement Metathesis

9 RCEYM/Transition-Metal-Catalyzed C–C Bond-Forming Processes

10 Conclusions

11 List of Acronyms



Publication History

Received: 31 July 2020

Accepted after revision: 29 September 2020

Publication Date:
09 November 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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