TY - JOUR
T1 - Total synthesis of naturally occurring furan compounds 5-{[(4- hydroxybenzyl)oxy]methyl}-2-furaldehyde and pichiafuran C
AU - Quiroz-Florentino, Héctor
AU - Hernández-Benitez, R. Israel
AU - Aviña, Judit A.
AU - Burgueño-Tapia, Eleuterio
AU - Tamariz, Joaquín
PY - 2011
Y1 - 2011
N2 - 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.
AB - 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.
KW - 5-(hydroxymethyl)-2-furaldehyde
KW - 5-{[(4-hydroxybenzyl)oxy]methyl}-2-furaldehyde
KW - Gastrodia elata Blume
KW - Pichia membranifaciens
KW - pichiafuran C
UR - http://www.scopus.com/inward/record.url?scp=79953026895&partnerID=8YFLogxK
U2 - 10.1055/s-0030-1258455
DO - 10.1055/s-0030-1258455
M3 - Artículo
SN - 0039-7881
SP - 1106
EP - 1112
JO - Synthesis (Germany)
JF - Synthesis (Germany)
IS - 7
ER -