Total synthesis of the natural succinate derivative of 5-(hydroxymethyl)furfural isolated from the Noni fruit (Morinda citrifolia).

Nat Prod Res. 2009;23(14):1355-62.

Quiroz-Florentino H, Garcia A, Burgueno-Tapia E, Tamariz J.

Departamento de Quimica Organica, Escuela Nacional de Ciencias Biologicas, Instituto Politecnico Nacional, 11340 Mexico, D.F., Mexico.


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.

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