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Recent Applications of the Horner-Wadsworth-Emmons Reaction to the Synthesis of Natural Products

[ Vol. 16 , Issue. 19 ]

Author(s):

Juan. A. Bisceglia and Liliana R. Orelli   Pages 2206 - 2230 ( 25 )

Abstract:


The Horner-Wadsworth-Emmons reaction has evolved in the last years as one of the most powerful and reliable method for stereocontrolled olefin synthesis. The reaction has become a widespread standard tool in natural products total syntheses, providing access to relatively simple as well as highly complex synthetic targets. In this work we present the most representative applications within the field of natural product synthesis from 2000 to the present year. The examples comprise the synthesis of macrocycles, 5 to 7 membered rings, lipids and related compounds, alkaloids and cyclic ethers. They were chosen from a large amount of literature reports and illustrate the use of the HWE reaction in the synthesis and elaboration of key intermediates and in the crucial assembly of highly functionalized synthetic precursors.

Keywords:

Horner-Wadsworth-Emmons (HWE) reaction, Carbonyl olefinations, Stabilized phosphonate carbanions, Natural products, Total synthesis, α, β-Unsaturated carbonyl compounds, Z-selectivity, N-(ω-formyl)substituted diethyl phosphonoacetamides, Intramolecular esterification, benzofuranone

Affiliation:

Departamento de Quimica Organica. Facultad de Farmacia y Bioquimica. Universidad de Buenos Aires. CONICET. Junin 956, (1113) Buenos Aires, Argentina.



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