title: Synthesis of β-Hydroxytyrosine, A Component of Burkholdines.
abstract: The preparation of four stereoisomers of β-hydroxytyrosine containing burkholdines is described. Enantio-pure syn β-hydroxytyrosine was synthesized using Sharpless aminohydroxylation. To obtain anti β-hydroxytyrosine, the cinnamate derivative was oxidized to give the optical active diol derivative by the AD-mix and subsequently, the a-hydroxy group was converted to amine. Deprotection of the acid-sensitive β-hydroxytyrosine derivatives was successively accomplished by brief immersion in 4N HCl/dioxane. All prepared stereoisomers of β-hydroxytyrosine were available for solid and solution phase peptide synthesis and amino acid analysis.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Konno
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Sasaki
authors.forename: Ryota
authors.initials: R
authors.lastname: Sato
authors.forename: XiuMei
authors.initials: X
authors.lastname: Zhu
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Otsuki
authors.forename: Megumi
authors.initials: M
authors.lastname: Ikoma
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry*; D004295:Dihydroxyphenylalanine / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000935:Antifungal Agents; D004295:Dihydroxyphenylalanine