A Convenient Synthesis of the Echinacea-Derived Immunostimulator and HIV-1 Integrase Inhibitor (−)-(2R,3R)-Chicoric Acid
✍ Scribed by Anne-Marie Lamidey; Lionel Fernon; Laurent Pouységu; Charlotte Delattre; Stéphane Quideau; Patrick Pardon
- Publisher
- John Wiley and Sons
- Year
- 2002
- Tongue
- German
- Weight
- 87 KB
- Volume
- 85
- Category
- Article
- ISSN
- 0018-019X
No coin nor oath required. For personal study only.
✦ Synopsis
The Echinacea-derived immunostimulator and HIV-1 integrase inhibitor (À)-chicoric acid ( 2,3-bis{[3-(3,4-dihydroxyphenyl)-1-oxoprop-2-enyl]oxy}butanedioic acid; 1a) was conveniently prepared via a silanepromoted 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.