- Asymmetric Synthesis of (2S,3R) β-(4-F-3-NO2) phenyl Serine, D-(R)-4-methoxy-3,5-Bis tButyldimethylsiloxy Phenylglycine and Their Assemblage to C-O-D Ring of Vancomycin
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The asymmetric synthesis of two appropriately functionalyzed 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 biary ether formation via intramolecular SNAr reaction led to the fully functionalized C-O-D ring vancomycin.
- Zhu, Jieping,Bouillon, Jean-Philippe,Singh, Girij Pal,Chastanet, Jacqueline,Beugelmans, Rene
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- Bis(5-aryl-2-pyridyl) derivatives
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A bis(5-aryl-2-pyridyl) compound represented by formula (1) or a salt thereof: wherein A is a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, and X is a group selected from the group consisting of moieties having formulas (2) to (5): wherein, in formula (2), m is an integer of 1 or 2; in formula (3), n is an integer of 1 to 6; and in formula (4), R is hydrogen or a lower alkyl group and p is an integer of 1 to 6.
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- Sulfinimine-mediated asymmetric synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine: The central amino acid of vancomycin and related agents
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The sulfinimine asymmetric Strecker synthesis, the addition of ethyl aluminum cyano alkoxide, 'EtAl(OR)CN' to sulfinimine 10, has been applied to a concise highly efficient four-step enantioselective synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine (3) and its derivatives in >97% ee. These epimerization-sensitive arylglycines are precursors of the key central amino acid of vancomycin and related glycopeptide antibiotics.
- Davis, Franklin A.,Fanelli, Dean L.
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p. 1981 - 1985
(2007/10/03)
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