Catechuic acid and ethyl 2,4,5-trihydroxybenzoate from D-glucose.
Synthesis of catechuic acid (1) and ethyl 2,4,5-trihydroxybenzoate (2) from D-glucose-derived beta-ketoester is described. The polyhydroxylated beta-ketoester obtained from the hydrolysis of sugar beta-ketoester 3 was subjected to an aldol-type condensation to get 4 that on enolization, dehydration, and hydrogenation afforded ethyl 2,4,5-trihydroxybenzoate (2). On the other hand, hydrogenation of aldol product 4 afforded polyhydroxylated keto-carbasugar 6, which on mild acid treatment and ester hydrolysis in basic media led to catechuic acid 1. Intermediate 4 is co-related to 3-dehydroshikimic acid, a biochemical intermediate from D-glucose in the synthesis of pro-catechuic acid.
Bhujbal
Namdeo N
NN
Garware Research Centre, Department of Chemistry, University of Pune, Pune 411007, India.
Bande
Omprakash P
OP
Dhavale
Dilip D
DD
D002392:Catechin / Q000138:chemical synthesis* / Q000737:chemistry; D005947:Glucose / Q000737:chemistry*; D062385:Hydroxybenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D062385:Hydroxybenzoates; D002392:Catechin; D005947:Glucose