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

Abstract

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.

Keywords:

• n-butyl (5-formylfuran-2-yl)methyl succinate
• 5-(hydroxymethyl)furfural
• D-fructose
• succinic anhydride
• Morinda citrifolia L.

Acknowledgements

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.