Total synthesis of naturally occurring furan compounds 5-{[(4- hydroxybenzyl)oxy]methyl}-2-furaldehyde and pichiafuran C

Héctor Quiroz-Florentino, R. Israel Hernández-Benitez, Judit A. Aviña, Eleuterio Burgueño-Tapia, Joaquín Tamariz

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16 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)1106-1112
Number of pages7
JournalSynthesis (Germany)
Issue number7
DOIs
StatePublished - 2011

Keywords

  • 5-(hydroxymethyl)-2-furaldehyde
  • 5-{[(4-hydroxybenzyl)oxy]methyl}-2-furaldehyde
  • Gastrodia elata Blume
  • Pichia membranifaciens
  • pichiafuran C

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