Journal
SYNTHESIS-STUTTGART
Volume -, Issue 7, Pages 1106-1112Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0030-1258455
Keywords
5-{[(4-hydroxybenzyl)oxy]methyl}-2-furaldehyde; pichiafuran C; 5-(hydroxymethyl)-2-furaldehyde; Gastrodia elata Blume; Pichia membranifaciens
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Funding
- SIP/IPN [20070339, 20080527, 20090519, 20100236]
- CONACYT [43508Q, 83446]
- SIP/IPN (PIFI)
- Ludwig K. Hellweg Foundation
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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.
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