Synthesis of the bis-diaryl ether fragment of vancomycin via enzymatic oxidative phenolic coupling

Tetrahedron Letters

Volumn 41, Issue 12, 2000, Pages 1907-1911

  Malnar, Ivica ^a   Sih, Charles J ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Biotransformations; Cross coupling reactions; Oxidative phenolic coupling; Peroxidase; Vancomycin

Indexed keywords

VANCOMYCIN; VANCOMYCIN DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0034681855     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00058-7     Document Type: Article

References (17)

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16. Compounds 2, 3, and 4 were prepared from (S)-tyrosine, (R)-4-hydroxyphenylglycine, and 4-hydroxybenzaldehyde, respectively, following published procedures. For the synthesis of (2S,3R)-methyl 2-(acetamido)-3-hydroxy-3-(3-chloro-4-hydroxyphenyl)propionate (2), and (2R, 3R)-methyl 2-(acetamido)-3-hydroxy-3-(3-chloro-4-hydroxyphenyl)propionate (4), see: Rao, A. V. R.; Chakraborty, T. K.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1994, 35, 5043-5046. For the synthesis of (2R)-methyl 2-(acetamido)-2-(3,5-dihalo-4-hydroxyphenyl)acetates (3), see: Pearson, A. J.; Chelliah, M. V.; Bignan, G. C. Synthesis 1997, 536-540.
17. Compounds 2, 3, and 4 were prepared from (S)-tyrosine, (R)-4-hydroxyphenylglycine, and 4-hydroxybenzaldehyde, respectively, following published procedures. For the synthesis of (2S,3R)-methyl 2-(acetamido)-3-hydroxy-3-(3-chloro-4-hydroxyphenyl)propionate (2), and (2R, 3R)-methyl 2-(acetamido)-3-hydroxy-3-(3-chloro-4-hydroxyphenyl)propionate (4), see: Rao, A. V. R.; Chakraborty, T. K.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1994, 35, 5043-5046. For the synthesis of (2R)-methyl 2-(acetamido)-2-(3,5-dihalo-4-hydroxyphenyl)acetates (3), see: Pearson, A. J.; Chelliah, M. V.; Bignan, G. C. Synthesis 1997, 536-540.