title: Short synthesis of 3-(hydroxymethyl)xylitol and structure revision of the anti-diabetic natural product from Casearia esculenta.
abstract: 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.
authors.affiliation: Research School of Chemistry, Australian National University , Canberra ACT 0200, Australia.
authors.forename: Ruomeng
authors.initials: R
authors.lastname: Wang
authors.forename: Michael N
authors.initials: MN
authors.lastname: Paddon-Row
authors.forename: Michael S
authors.initials: MS
authors.lastname: Sherburn
mesh_terms: D000818:Animals; D001688:Biological Products; D037821:Casearia / Q000737:chemistry*; D003921:Diabetes Mellitus, Experimental / Q000188:drug therapy*; D007004:Hypoglycemic Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D008099:Liver / Q000737:chemistry* / Q000187:drug effects*; D015394:Molecular Structure; D010936:Plant Extracts / Q000032:analysis* / Q000737:chemistry* / Q000302:isolation & purification; D018517:Plant Roots / Q000737:chemistry*; D051381:Rats; D013237:Stereoisomerism; D014993:Xylitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: C532178:3-hydroxymethylxylitol; D001688:Biological Products; D007004:Hypoglycemic Agents; D010936:Plant Extracts; D014993:Xylitol