CC BY-NC-ND 4.0 · Synthesis 2021; 53(16): 2713-2739
DOI: 10.1055/a-1493-6331
review

Applications of the Horner–Wadsworth–Emmons Olefination in Modern Natural Product Synthesis

,
Maria Sauer
,
We greatly acknowledge funding from the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation program (Project: 802736 MORPHEUS) and Boehringer Ingelheim Stiftung (Exploration Grant Engina).


Abstract

The Horner–Wadsworth–Emmons (HWE) reaction is one of the most reliable olefination reaction and can be broadly applied in organic chemistry and natural product synthesis with excellent selectivity. Within the last few years HWE reaction conditions have been optimized and new reagents developed to overcome challenges in the total syntheses of natural products. This review highlights the application of HWE olefinations in total syntheses of structurally different natural products covering 2015 to 2020. Applied HWE reagents and reactions conditions are highlighted to support future synthetic approaches and serve as guideline to find the best HWE conditions for the most complicated natural products.

1 Introduction and Historical Background

2 Applications of HWE

2.1 Cyclization by HWE Reactions

2.2.1 Formation of Medium- to Larger-Sized Rings

2.2.2 Formation of Small- to Medium-Sized Rings

2.3 Synthesis of α,β-Unsaturated Carbonyl Groups

2.4 Synthesis of Substituted C=C Bonds

2.5 Late-Stage Modifications by HWE Reactions

2.6 HWE Reactions on Solid Supports

2.7 Synthesis of Poly-Conjugated C=C Bonds

2.8 HWE-Mediated Coupling of Larger Building Blocks

2.9 Miscellaneous

3 Summary and Outlook



Publication History

Received: 20 January 2021

Accepted after revision: 28 April 2021

Accepted Manuscript online:
28 April 2021

Article published online:
24 June 2021

© 2021. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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