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Synthesis 2011(7): 1106-1112  
DOI: 10.1055/s-0030-1258455
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Héctor Quiroz-Florentinoa, R. Israel Hernández-Beniteza, Judit A. Aviñaa,b, Eleuterio Burgueño-Tapiaa, Joaquín Tamariz*a
a Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, 11340 México, D.F., Mexico
Fax: +52(55)57296300/46211; e-Mail: jtamariz@woodward.encb.ipn.mx;
b Instituto de Investigaciones Quimicobiológicas, Universidad Michoacana de San Nicolas de Hidalgo, Edif. B-1, Ciudad Universitaria, Francisco J. Mujica s/n, 58066 Morelia, Mich., Mexico
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Publication History

Received 5 November 2010
Publication Date:
01 March 2011 (online)

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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.

Key words

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

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