title: Total Synthesis of Ustiloxin D Utilizing an Ammonia-Ugi Reaction.
abstract: Total synthesis of the highly functionalized cyclic peptide natural product, ustiloxin D, has been achieved in a convergent manner. Our strategy incorporates an asymmetric allylic alkylation to construct the tert-alkyl aryl ether linkage between the dopa and isoleucine residues. The elaborated β-hydroxydopa derivative is rapidly converted to a linear tripeptide through an ammonia-Ugi reaction. Subsequent cyclization and global deprotection affords ustiloxin D in six steps from a known β-hydroxydopa derivative.
authors.affiliation: School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne , Parkville, VIC 3010, Australia.
authors.forename: Aaron L
authors.initials: AL
authors.lastname: Brown
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.affiliation: School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne , Parkville, VIC 3010, Australia.
authors.forename: Craig A
authors.initials: CA
authors.lastname: Hutton
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000478:Alkylation; D000641:Ammonia / Q000737:chemistry*; D008968:Molecular Conformation; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D010456:Peptides, Cyclic; C089079:ustiloxin D; D000641:Ammonia