Total Synthesis of Ustiloxin D Utilizing an Ammonia-Ugi Reaction
Aaron L Brown, Quentin I Churches, Craig A Hutton
JOURNAL OF ORGANIC CHEMISTRY | AMER CHEMICAL SOC | Published : 2015
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.
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The Australian Research Council is acknowledged for support.