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Optimization of the Ugi Reaction Using Parallel Synthesis and Automated Liquid Handling
Published on: November 11, 2008
Total Synthesis of Ustiloxin D Utilizing an Ammonia-Ugi Reaction
Aaron L Brown1, Quentin I Churches1, Craig A Hutton1
1School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne , Parkville, VIC 3010, Australia.
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.
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