De novo synthesis of aceric acid and an aceric acid building block.
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.
Timmer
Mattie S M
MS
Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zürich, Wolfgang-Pauli Strasse 10, 8093 Zurich, Switzerland.
Stocker
Bridget L
BL
Seeberger
Peter H
PH
D010944:Plants / Q000737:chemistry; D013400:Sugar Acids / Q000138:chemical synthesis*; D013865:Thioglycosides / Q000138:chemical synthesis; D014994:Xylose / Q000031:analogs & derivatives* / Q000138:chemical synthesis
C511260:3-C-carboxy-5-deoxyxylose; D013400:Sugar Acids; D013865:Thioglycosides; D014994:Xylose