title: De novo synthesis of aceric acid and an aceric acid building block.
abstract: The de novo synthesis of an aceric acid thioglycoside building block and the total synthesis of the plant carbohydrate aceric acid are described via a highly convergent strategy. Aldol reaction of acetaldehyde and a protected tartaric acid derivative provided the open chain carbohydrate. Subsequent acid treatment yielded the aceric acid thioglycoside in 35% total yield over five steps. Oxidative cleavage of the thioketal in the open chain carbohydrate and basic hydrolysis of the methyl ester furnished fully deprotected aceric acid in 31% yield over six steps.
authors.affiliation: Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zürich, Wolfgang-Pauli Strasse 10, 8093 Zurich, Switzerland.
authors.forename: Mattie S M
authors.initials: MS
authors.lastname: Timmer
authors.forename: Bridget L
authors.initials: BL
authors.lastname: Stocker
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
mesh_terms: D010944:Plants / Q000737:chemistry; D013400:Sugar Acids / Q000138:chemical synthesis*; D013865:Thioglycosides / Q000138:chemical synthesis; D014994:Xylose / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: C511260:3-C-carboxy-5-deoxyxylose; D013400:Sugar Acids; D013865:Thioglycosides; D014994:Xylose