title: Synthesis of tubuphenylalanines via Ireland-Claisen rearrangement.
abstract: The Ireland-Claisen rearrangement is the central step in the synthesis of tubuphenylalanine, a key building block of the highly antitumor-active tubulysins. The rearrangement of substituted β-amino acid allyl esters, in combination with subsequent decarboxylation and oxidative cleavage of the double bond, allows the highly stereoselective introduction of substituents into the α-position of the resulting γ-amino acids.
authors.affiliation: Institute for Organic Chemistry, Saarland University, Building C4.2, D-66123 Saarbruecken, Germany.
authors.forename: Dominic
authors.initials: D
authors.lastname: Becker
authors.forename: Uli
authors.initials: U
authors.lastname: Kazmaier
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D010649:Phenylalanine / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D004952:Esters; D009842:Oligopeptides; D010649:Phenylalanine