Short synthesis of 3-(hydroxymethyl)xylitol and structure revision of the anti-diabetic natural product from Casearia esculenta.

3-(Hydroxymethyl)xylitol, a compound reportedly isolated from the root of Casearia esculenta (Roxb.), along with its three possible stereoisomers, has been synthesized for the first time by way of a triple dihydroxylation reaction performed upon the simplest cross-conjugated hydrocarbon, [3]dendralene. The data for the natural product do not match any of the isomeric 3-(hydroxymethyl)pentitols. The structure of the natural product from the root of Casearia esculenta (Roxb.) has been corrected by reanalysis of the published data.