Recent applications of the Horner-Wadsworth-Emmons reaction to the synthesis of natural products

The Horner-Wadsworth-Emmons reaction has evolved in the last years as one of the most powerful and reliable method for stereo controlled olefin synthesis. The reaction has become a widespread standard tool in natural products total syntheses, providing access to relatively simple as well as highly c...

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Detalhes bibliográficos
Autores: Bisceglia, Juan Angel, Orelli, Liliana Raquel
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2012
País:Argentina
Recursos:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/198365
Acesso em linha:http://hdl.handle.net/11336/198365
Access Level:acceso abierto
Palavra-chave:Α,Β-UNSATURATED CARBONYL COMPOUNDS
CARBONYL OLEFINATIONS
HORNER-WADSWORTH-EMMONS (HWE) REACTION
NATURAL PRODUCTS
STABILIZED PHOSPHONATE CARBANIONS
TOTAL SYNTHESIS
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Descrição
Resumo:The Horner-Wadsworth-Emmons reaction has evolved in the last years as one of the most powerful and reliable method for stereo controlled 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.