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A Convenient Synthesis of the Echinacea-Derived Immunostimulator and HIV-1 Integrase Inhibitor (−)-(2R,3R)-Chicoric Acid
Document Type
Article
Source
Helvetica Chimica Acta; August 2002, Vol. 85 Issue: 8 p2328-2334, 7p
Subject
Language
ISSN
0018019X; 15222675
Abstract
The Echinacea-derived immunostimulator and HIV-1 integrase inhibitor (−)-chicoric acid (=2,3-bis{[3-(3,4-dihydroxyphenyl)-1-oxoprop-2-enyl]oxy}butanedioic acid; 1a) was conveniently prepared via a silane-promoted Pd-mediated chemoselective hydrogenolysis of its perbenzylated derivative 12a, which was generated from an efficient and reliable carbodiimide-mediated coupling reaction between the caffeic acid dibenzyl ether derivative 7 and commercially available (+)-dibenzyl L-tartrate (9a). The other naturally occurring dextrorotatory chicoric acid (1b) can be similarly prepared.