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A Convenient Synthesis of the Echinacea ‐Derived Immunostimulator and HIV‐1 Integrase Inhibitor (−)‐(2 R ,3 R )‐Chicoric Acid
Author(s) -
Lamidey AnneMarie,
Fer Lionel,
Pouységu Laurent,
Delattre Charlotte,
Quideau Stéphane,
Pardon Patrick
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200208)85:8<2328::aid-hlca2328>3.0.co;2-x
Subject(s) - chemistry , integrase , derivative (finance) , integrase inhibitor , caffeic acid , stereochemistry , orcinol , ether , combinatorial chemistry , disiloxane , organic chemistry , human immunodeficiency virus (hiv) , catalysis , biochemistry , medicine , antiretroviral therapy , viral load , family medicine , financial economics , economics , gene , antioxidant
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.