Facile syntheses of (2R,3R)-(-)- and (2S,3S)-(+)-chicoric acids

Synthetic Communications

Volumn 28, Issue 4, 1998, Pages 737-740

  Zhao, He ^a   Burke Jr , Terrence R ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 BIS[[(3,4 DIHYDROXYPHENYL) 1 OXO 2 PROPENYL]OXY]BUTANEDIOIC ACID; CICHORIC ACID; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; PLANT; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0031905222     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808005946     Document Type: Article

References (9)

1. Scarpati, M. L.; Oriente, G. Tetrahedron 1958, 4, 43-48.
2. Robinson, W. E., Jr.; Cordeiro, M.; Abdel-Malek, S.; Jia, Q.; Chow, S. A.; Reinecke, M. G.; Mitchell, W. M. Mol. Pharm. 1996, 50, 846-855.
3. Robinson, W. E., Jr.; Reinecke, M. G.; Abdel-Malek, S.; Jia, Q.; Chow, S. A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 6326-6331. (No experimental details were provided for the synthesis of L-chicoric acid.)
4. Zhao, H.; Neamati, N.; Mazumder, A.; Sunder, S.; Pommier, Y.; Terrence R. Burke, Jr. J. Med. Chem. 1997, 40, 1186-1194.
5. Compound 5 has been previously prepared (for example: Haslam, E.; Makinson, G. K.; Naumann, M. O.; Cunningham, J. J. Chem. Soc. 1964, 2137.) It is easily synthesized on large scale by treatment of 3,4-dihydroxycinnamic acid with acetic anhydride (10 equivalents) in pyridine (v/v = 5:1) in the dark overnight at room temperature. Upon removal of solvent, residue is crystallized from EtOAc:hexane to provide diacetyl caffeic acid as a white solid. Reflux (3 h) with thionyl chloride (5 equivalents) in benzene (v/v = 8:1) provides 5 upon removal of solvent.
6. 16: C, 60.47; H, 5.61. Found: C, 60.38; H, 5.65.
7. 16: C, 56.08; H, 4.08. Found: C, 55.82; H, 4.17.
8. 2O: C, 52.23; H, 4.28. Found: C, 52.07; H, 4.33.
9. D +340° (MeOH, c 0.14). Other physical data were identical to that displayed by 2.