Synthetic studies toward mannopeptimycin-E: synthesis of the O-linked tyrosine 1,4-alpha,alpha-manno,manno-pyranosyl pyranoside.
[structure: see text] The enantioselective synthesis of the C-4' acylated 1,4-alpha,alpha-manno,manno-disaccharide fragment of mannopeptimycin-E has been achieved in seven steps from d-tyrosine. The route relies upon diastereoselective palladium-catalyzed glycosylation, diastereoselective reduction, and diastereoselective bis-dihydroxylation. The efficiency of the synthesis is demonstrated by the high overall yield (37%) and the preparation of various analogues.
Babu
Ravula Satheesh
RS
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Guppi
Sanjeeva R
SR
O'Doherty
George A
GA
D002384:Catalysis; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D014443:Tyrosine / Q000737:chemistry*
D006020:Glycopeptides; C478082:mannopeptimycin; C516133:mannopeptimycin-E; D014443:Tyrosine; D010165:Palladium