TY - JOUR
T1 - Total synthesis of the natural succinate derivative of 5-(hydroxymethyl) furfural isolated from the Noni fruit (Morinda citrifolia)
AU - Quiroz-Florentino, Hector
AU - García, Abraham
AU - Burgueño-Tapia, Eleuterio
AU - Tamariz, Joaquín
N1 - Funding Information:
J. Tamariz acknowledges SIP/IPN (Grants 20060583, 20070339, 20080527 and 20090519) and CONACYT (Grants 43508Q and 83446) for financial support. H. Quiroz-Florentino thanks CONACYT for awarding a graduate scholarship, and also SIP/IPN (PIFI) for a scholarship complement. A. García thanks CONACYT for a postdoctoral fellowship awarded. E. Burgueño-Tapia and J. Tamariz are fellows of the EDI-IPN and COFAA-IPN programs.
PY - 2009/9
Y1 - 2009/9
N2 - Three alternative synthetic routes for the synthesis of naturally occurring n-butyl (5-formylfuran-2-yl)methyl succinate (1) are described. One of them started from furfuryl alcohol (4), and the other two synthetic strategies started from 5-(hydroxymethyl)furfural (6), which could be readily obtained from D-fructose. One of the latter involved a two-step reaction sequence: esterification of 6 with succinic anhydride (5) and esterification of the resultant mono-succinate 2 with n-butyl bromide, to give 1 in 85% overall yield. The second, a one-pot two-step synthesis, consisted of treating 6 with 5 followed by the addition of n-butyl bromide to afford the desired natural product 1 in 85% yield.
AB - Three alternative synthetic routes for the synthesis of naturally occurring n-butyl (5-formylfuran-2-yl)methyl succinate (1) are described. One of them started from furfuryl alcohol (4), and the other two synthetic strategies started from 5-(hydroxymethyl)furfural (6), which could be readily obtained from D-fructose. One of the latter involved a two-step reaction sequence: esterification of 6 with succinic anhydride (5) and esterification of the resultant mono-succinate 2 with n-butyl bromide, to give 1 in 85% overall yield. The second, a one-pot two-step synthesis, consisted of treating 6 with 5 followed by the addition of n-butyl bromide to afford the desired natural product 1 in 85% yield.
KW - 5-(hydroxymethyl)furfural
KW - D-fructose
KW - Morinda citrifolia L
KW - N-butyl (5-formylfuran-2-yl)methyl succinate
KW - Succinic anhydride
UR - http://www.scopus.com/inward/record.url?scp=70449122620&partnerID=8YFLogxK
U2 - 10.1080/14786410903040477
DO - 10.1080/14786410903040477
M3 - Artículo
SN - 1478-6419
VL - 23
SP - 1355
EP - 1362
JO - Natural Product Research
JF - Natural Product Research
IS - 14
ER -