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.