Journal article

Total Synthesis of Ustiloxin D Utilizing an Ammonia-Ugi Reaction

AL Brown, QI Churches, CA Hutton

Journal of Organic Chemistry | Published : 2015

DOI: 10.1021/acs.joc.5b01519

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.

University of Melbourne Researchers

Craig Hutton Author

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Grants

Awarded by Australian Research Council

Funding Acknowledgements

The Australian Research Council is acknowledged for support.

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24Web of Science

Keywords

3405 Organic Chemistry

False Smut Balls

34 Chemical Sciences

Science & Technology

Natural-Products

Physical Sciences

Multicomponent Reactions

Chemistry, Organic