Asymmetric synthesis of (2S,3R) β-(4-F-3-NO2) phenyl serine, D-(R)-4-methoxy-3,5-bistbutyldimethylsiloxy phenylglycine and their assemblage to C-O-D ring of vancomycin

Artigo Revisado por pares

Asymmetric synthesis of (2S,3R) β-(4-F-3-NO2) phenyl serine, D-(R)-4-methoxy-3,5-bistbutyldimethylsiloxy phenylglycine and their assemblage to C-O-D ring of vancomycin

1995; Elsevier BV; Volume: 36; Issue: 39 Linguagem: Inglês

10.1016/0040-4039(95)01409-b

ISSN

1873-3581

Autores

Jieping Zhu, Jean‐Philippe Bouillon, Girij Pal Singh, J. CHASTANET, René Bengelmans,

Tópico(s)

Synthetic Organic Chemistry Methods

Resumo

The asymmetric synthesis of two appropriately functionalized non-proteinogenic amino acids 2 and 3 needed for the total synthesis of vancomycin was described. The assemblage of these amino acids into linear tripeptide followed by biaryl ether formation via intramolecular SNAr reaction led to the fully functionalized C-O-D ring of vancomycin.

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Asymmetric synthesis of (2S,3R) β-(4-F-3-NO2) phenyl serine, D-(R)-4-methoxy-3,5-bistbutyldimethylsiloxy phenylglycine and their assemblage to C-O-D ring of vancomycin