A Convenient Synthesis of the Echinacea-Derived Immunostimulator and HIV-1 Integrase Inhibitor (−)-(2R,3R)-Chicoric Acid
2002; Wiley; Volume: 85; Issue: 8 Linguagem: Inglês
10.1002/1522-2675(200208)85
ISSN1522-2675
AutoresAnne‐Marie Lamidey, Lionel Fernon, Laurent Pouységu, Charlotte Delattre, Stéphane Quideau, Patrick Pardon,
Tópico(s)Pediatric health and respiratory diseases
ResumoThe 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.
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