title: Decarbonylative approach to the synthesis of enamides from amino acids: stereoselective synthesis of the (Z)-aminovinyl-D-cysteine unit of mersacidin.
abstract: The Pd- and Ni-promoted decarbonylation of amino acid thioesters proceeds smoothly to yield enamides. The synthesis of the (S)-(Z)-AviMeCys subunit of mersacidin, an MRSA-active lantibiotic, via this approach, is described.
authors.affiliation: Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47505, USA.
authors.forename: Pablo
authors.initials: P
authors.lastname: García-Reynaga
authors.forename: Angela K
authors.initials: AK
authors.lastname: Carrillo
authors.forename: Michael S
authors.initials: MS
authors.lastname: VanNieuwenhze
mesh_terms: D000577:Amides / Q000737:chemistry*; D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D001430:Bacteriocins / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry; D008969:Molecular Sequence Data; D009532:Nickel / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D010455:Peptides / Q000737:chemistry*; D050050:Protein Carbonylation; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis*
chemical_list: D000577:Amides; D000596:Amino Acids; D001430:Bacteriocins; D010455:Peptides; D014753:Vinyl Compounds; C069959:mersacidin; D010165:Palladium; D009532:Nickel; D003545:Cysteine