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

Dávid Roman; Maria Sauer; Christine Beemelmanns

doi:10.1055/a-1493-6331

Synthesis, Table of Contents

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

Dávid Roman

,

Maria Sauer

,

Christine Beemelmanns ∗

Abstract

All articles of this category

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

Key words

HWE reaction - olefination - C=C bond formation - phosphonate - aldehyde - alkenes - natural products

Full Text

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