Total synthesis of mycocyclosin

JR Cochrane; JM White; U Wille; CA Hutton

Journal article

Total synthesis of mycocyclosin

JR Cochrane, JM White, U Wille, CA Hutton

Organic Letters | Published : 2012

DOI: 10.1021/ol300831t

Abstract

The first total synthesis of mycocyclosin, a diketopiperazine natural product isolated from M. tuberculosis, is described. While direct oxidative coupling of tyrosine phenolic groups was unsuccessful, construction of the highly strained bicyclic framework was successfully accomplished through an intramolecular Miyaura-Suzuki cross-coupling to generate the biaryl linkage. © 2012 American Chemical Society.

University of Melbourne Researchers

Jonathan White Author

Uta Wille Author

Craig Hutton Author

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Grants

Awarded by Australian Research Council

Funding Acknowledgements

Financial support from the Australian Research Council (DP110100112) is acknowledged. This work was supported by the National Computing Infrastructure (NCI) facility. Dr. Ian Luck (University of Sydney) is thanked for assistance with VT NMR experiments. Assoc. Prof. Spencer Williams (University of Melbourne) is thanked for bringing this compound to our attention.