Total synthesis of the natural succinate derivative of 5-(hydroxymethyl)furfural isolated from the Noni fruit (Morinda citrifolia).
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.
Quiroz-Florentino
Hector
H
Departamento de Quimica Organica, Escuela Nacional de Ciencias Biologicas, Instituto Politecnico Nacional, 11340 Mexico, D.F., Mexico.
Garcia
Abraham
A
Burgueno-Tapia
Eleuterio
E
Tamariz
Joaquin
J
D005638:Fruit / Q000737:chemistry*; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D032066:Morinda / Q000737:chemistry*; D013386:Succinates / Q000138:chemical synthesis* / Q000737:chemistry*; D019802:Succinic Acid / Q000737:chemistry*
D013386:Succinates; C008046:5-hydroxymethylfurfural; D019802:Succinic Acid; D005662:Furaldehyde; C041105:monomethyl succinate