A four-step synthesis of erythro-m-chloro-3-hydroxytyrosine ethyl ester enantiomerically pure

Tetrahedron Letters

Volumn 39, Issue 15, 1998, Pages 2191-2194

  Solladié Cavallo, Arlette ^a   Nsenda, Thomas ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 CHLORO 3 HYDROXYTYROSINE; 3 CHLORO 3 HYDROXYTYROSINE ETHYL ESTER; ANTIBIOTIC AGENT; ARIDICIN A; ESTER DERIVATIVE; GLYCINE DERIVATIVE; TITANIUM; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG; VANCOMYCIN;

ARTICLE; CHIRALITY; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032499050     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00172-5     Document Type: Article

References (21)

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8. 5) Discovered by Wagner in 1894 (Ber. Chem. Gessels.,27, 2272), hydroxypinanone 2 was then described and studied by Delépine M. et al. (Bull. Soc. Chim. Fr. 1937, 4, 1669) and Kuwata (J. Am. Chem. Soc. 1937, 59, 2509). Hydroxypinanone was used for the first time as chiral auxiliary by Yamada S.I., Shioiri T et al. in 1976 (ref. 6).
9. 5) Discovered by Wagner in 1894 (Ber. Chem. Gessels.,27, 2272), hydroxypinanone 2 was then described and studied by Delépine M. et al. (Bull. Soc. Chim. Fr. 1937, 4, 1669) and Kuwata (J. Am. Chem. Soc. 1937, 59, 2509). Hydroxypinanone was used for the first time as chiral auxiliary by Yamada S.I., Shioiri T et al. in 1976 (ref. 6).
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14. 4, traces of the isopropyl ester corresponding to 5I and having the same configuration is also observed due to trans-esterification (∼5%).
15. 3/TMS) : 180.6, 170.4, 153.8, 136.5, 134.2, 129.1, 128.7, 128.0, 127.1, 126.5, 122.9, 113.4, 76.8, 73.8, 70.8, 68.3, 61.4, 50.3, 38.6, 38.3, 34.1, 28.3, 28.0, 27.3, 22.8, 14.2.
16. 3/TMS) : 173.0, 153.9, 136.4, 133.5, 128.6, 128.5, 128.0, 127.1, 125.7, 123.2, 73.3, 70.9, 61.4, 59.8, 14.2.
17. 3J=7).
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21. 2 : C%, 44.61 ; H%, 5.11. Found : C%, 44.52 ; H%, 5.17.