Total Synthesis of Naturally Occurring Furan Compounds 5-{[(4-Hydroxybenzyl)oxy]methyl}-2-furaldehyde and Pichiafuran C

Autor:	R. Israel Hernández-Benitez, Héctor Quiroz-Florentino, Judit A. Aviña, Eleuterio Burgueño-Tapia, Joaquín Tamariz
Rok vydání:	2011
Předmět:	chemistry.chemical_classification Furaldehyde Organic Chemistry Total synthesis Furfural Chemical synthesis Aldehyde Catalysis chemistry.chemical_compound chemistry Aldose Furan Organic chemistry Hydroxymethyl
Zdroj:	Synthesis. 2011:1106-1112
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0030-1258455
Popis:	The synthesis of the natural furan derivatives 5-{[(4-hydroxybenzyl)oxy]methyl}-2-furaldehyde and pichiafuran C is described. Diverse alternative synthetic approaches were developed for the preparation of these natural products. They were prepared through an etherification reaction of the key furan precursor 5-(hydroxymethyl)-2-furaldehyde (HMF), which can be readily obtained from D -fructose, D-glucose, or sucrose, with the corresponding alcohols. 5-{[(4-Hydroxybenzyl)oxy]methyl}-2-furaldehyde was not only obtained in a two-step methodology but also by a biomimetic single-step synthesis. Similarly, pichiafuran C was prepared by three different syntheses, each one by a two-step procedure, also including a biomimetic approach.
Databáze:	OpenAIRE
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