title: Synthesis of β,γ-dihydroxyhomotyrosines by a tandem Petasis-asymmetric dihydroxylation approach.
abstract: Petasis reactions of substituted styrenylboronic acids and glyoxylic acid, employing tert-butylsulfinamide as the 'amine' component, proceed with high stereoselectivity to produce β,γ-dehydrohomoarylalanine derivatives. Subsequent asymmetric dihydroxylation under neutral conditions gives the corresponding protected β,γ-dihydroxyhomoarylalanines with up to 15:1 dr. The method has been exploited in the efficient, stereoselective synthesis of protected β,γ-dihydroxyhomotyrosine, a component of the antifungal cyclic peptide echinocandin B.
authors.affiliation: School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, VIC 3010, Australia.
authors.forename: Quentin I
authors.initials: QI
authors.lastname: Churches
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: White
authors.forename: Craig A
authors.initials: CA
authors.lastname: Hutton
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D054714:Echinocandins / Q000138:chemical synthesis* / Q000737:chemistry; D005656:Fungal Proteins / Q000138:chemical synthesis* / Q000737:chemistry; D006038:Glyoxylates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000935:Antifungal Agents; D054714:Echinocandins; D005656:Fungal Proteins; D006038:Glyoxylates; D014443:Tyrosine; C013947:3,4-dihydroxyhomotyrosine; C007572:echinocandin B; C031150:glyoxylic acid