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Synthesis 2018; 50(19): 3749-3786
DOI: 10.1055/s-0037-1610206
review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Total Synthesis via Metathesis Reactions

Iván Cheng-Sánchez
Department of Organic Chemistry, Faculty of Sciences, University of Málaga, Campus de Teatinos s/n. 29071-Málaga, Spain   Email: frsarabia@uma.es
,
Francisco Sarabia*
Department of Organic Chemistry, Faculty of Sciences, University of Málaga, Campus de Teatinos s/n. 29071-Málaga, Spain   Email: frsarabia@uma.es
› Author AffiliationsThis work was supported financially by the Ministerio de Economía y Competitividad (MINECO) (Reference CTQ2014-60223-R)
Further Information

Publication History

Received: 16 April 2018

Accepted after revision: 30 May 2018

Publication Date:
18 July 2018 (online)

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Abstract

The metathesis reactions, in their various versions, have become a powerful and extremely valuable tool for the formation of carbon–carbon bonds in organic synthesis. The plethora of available catalysts to perform these reactions, combined with the various transformations that can be accomplished, have positioned the metathesis processes as one of the most important reactions of this century. In this review, we highlight the most relevant synthetic contributions published between 2012 and early 2018 in the field of total synthesis, reflecting the state of the art of this chemistry and demonstrating the significant synthetic potential of these methodologies.

1 Introduction

2 Alkene Metathesis in Total Synthesis

2.1 Total Synthesis Based on a Ring-Closing-Metathesis Reaction

2.2 Total Synthesis Based on a Cross-Metathesis Reaction

2.3 Strategies for Selective and Efficient Metathesis Reactions of Alkenes

2.3.1 Temporary Tethered Ring-Closing Metathesis

2.3.2 Relay Ring-Closing Metathesis

2.3.3 Stereoselective Alkene Metathesis

2.3.4 Alkene Metathesis in Tandem Reactions

3 Enyne Metathesis in Total Synthesis

3.1 Total Syntheses Based on a Ring-Closing Enyne-Metathesis Reaction

3.2 Total Syntheses Based on an Enyne Cross-Metathesis Reaction

3.3 Enyne Metathesis in Tandem Reactions

4 Alkyne Metathesis in Total Synthesis

4.1 Total Synthesis Based on a Ring-Closing Alkyne-Metathesis Reaction

4.2 Other Types of Alkyne-Metathesis Reactions

5 Conclusions

Key words

alkene metathesis - alkyne metathesis - enyne metathesis - natural products - total synthesis