Syntheses of the syn and anti α-amino-β-hydroxy acids of vancomycin: (2S, 3R) and (2R, 3R) p-chloro-3-hydroxytyrosines

Tetrahedron Letters

Volumn 37, Issue 44, 1996, Pages 7967-7970

  Girard, Anne ^a   Greck, Christine ^a   Ferroud, Didier ^b   Genêt, Jean Pierre ^a  

^a Lab de Bioorganique et B   (France)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYAMINO ACID; TYROSINE DERIVATIVE; VANCOMYCIN;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030605052     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01829-1     Document Type: Article

References (26)

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2. 1 - McCormick, M.H.; Stark, W.M.; Pittenger, G.F.; Pittenger, R.C.; McGuire, G.M. Antibiot. Annual 1955-1956, Medicinal Encyclopedia, Inc.: New York, 1956; pp 606-611. Rao, A.V.R.; Gurjar, M.K.; Reddy, K.L.; Rao, A.S. Chem. Rev. 1995, 95, 2135-2167 and references cited therein.
3. 2 - Evans, D.A.; Ellman, J.A.; De Vries, K.M. J. Am. Chem. Soc. 1989, 111, 8912-8914.
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6. 4 - See ref. 2. Previously described methodology: Evans, D.A.; Weber, A.E. J. Am. Chem. Soc. 1986, 108, 6757-6761. Evans, D.A.; Weber, A.E. ibid 1987, 109, 7151-7157. Evans, D.A.; Sjogren, E.B.; Weber, A.E.; Conn, R.E. Tetrahedron Lett. 1987, 28, 39-42.
7. 4 - See ref. 2. Previously described methodology: Evans, D.A.; Weber, A.E. J. Am. Chem. Soc. 1986, 108, 6757-6761. Evans, D.A.; Weber, A.E. ibid 1987, 109, 7151-7157. Evans, D.A.; Sjogren, E.B.; Weber, A.E.; Conn, R.E. Tetrahedron Lett. 1987, 28, 39-42.
8. 4 - See ref. 2. Previously described methodology: Evans, D.A.; Weber, A.E. J. Am. Chem. Soc. 1986, 108, 6757-6761. Evans, D.A.; Weber, A.E. ibid 1987, 109, 7151-7157. Evans, D.A.; Sjogren, E.B.; Weber, A.E.; Conn, R.E. Tetrahedron Lett. 1987, 28, 39-42.
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12. 6 - Chong, J.M.; Sharpless, K.B. J. Org. Chem. 1985, 50, 1560-1563. Pons, D.; Savignac, M.; Genêt, J.P. Tetrahedron Lett. 1990, 31; 5023-5026. Genêt, J.P.; Durand, J.O.; Savignac, M.; Pons, D. ibid 1992, 33, 2497-2500.
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14. 7 - Genêt, J.P.; Jugé, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765-6768. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553-5562. Gautshi, M.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1992, 31, 1083-1085.
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16. 8 - Genêt, J.P.; Mallart, S.; Jugé, S.; Laffite, J.A. French Patent n°8911159, Aug. 1989.
17. Genêt, J.P.; Pinel, C.; Mallart, S.; Jugé, S.; Thorimbert, S.; Laffitte, J.A. Tetrahedron: Asymmetry 1991, 2, 555-567.
18. Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Takemoti, H.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134-9135.
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24. 20= +5 (c=0.3, EtOH).
25. 13 - Alexakis, A.; Lensen, N.; Mangeney, P. Synlett 1991, 625-626.
26. 20= -25 (C= 1, EtOH).