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. doi: 10.1080/14786410903040477.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fruit / chemistry*
  • Furaldehyde / analogs & derivatives*
  • Furaldehyde / chemistry
  • Molecular Structure
  • Morinda / chemistry*
  • Succinates / chemical synthesis*
  • Succinates / chemistry*
  • Succinic Acid / chemistry*

Substances

  • Succinates
  • 5-hydroxymethylfurfural
  • Succinic Acid
  • Furaldehyde
  • monomethyl succinate