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The synthesis of 2-(E)-O-(4-hydroxy-cinnamoyl)-ᴅ,ʟ-galactaric acid (1a) is described. Starting with free galactaric acid (2) and 4-acetoxy-cinnamoyl-chloride (3), these compounds were esterified under regioselective conditions to racemic 2-(E)-O-(4-acetoxy-cinnamoyl)-galactaric acid (4). After deprotection of the p-coumaroyl moiety 1a was obtained as a photo-unstable product. Optical resolution of racemate l a on bovine serum albumin covalently bound to silica resulted in the isolation of the pure optical isomers. The (+)-dextrorotatory synthetic enantiomer l a proved to be identical with the natural factor.

zeitschrift für naturforschung c

Pflanzenabwehrstoffe XXXIV [1]. Synthese der 2-(E)-O-(4-Hydroxy-cinnamoyI)-ᴅ,ʟ-galactarsäure, eines vermeintlich photosensitiven Faktors aus Glycine max / Synthesis of 2-(E)-O-(4-Hydroxy-cinnamoyl)-ᴅ,ʟ-galactaric Acid, a Presumptive Photosensitive Factor from Glycine max