Total Syntheses of Linear Poly-Thiazole/Oxazole Plantazolicin A and its biosynthetic precursor Plantazolicin B
Angewandte Chemie International Edition
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Wilson, Z., Fenner, S., & Ley, S. (2014). Total Syntheses of Linear Poly-Thiazole/Oxazole Plantazolicin A and its biosynthetic precursor Plantazolicin B. Angewandte Chemie International Edition, 54 1284-1288. https://doi.org/10.1002/anie.201410063
Plantazolicin A, a linear decacyclic natural product, exhibits desirable selective activity against the causative agent of anthrax toxicity. The total synthesis of plantazolicin A and its biosynthetic precursor plantazolicin B was successfully achieved via an efficient, unified and highly convergent route featuring dicyclisations to form 2,4-concatenated oxazoles and the mild synthesis of thiazoles from natural amino acids. This report represents the first synthesis of plantazolicin B and includes the first complete characterization data for both natural products.
cyclization, heterocycles, natural products, peptides, total synthesis
We gratefully acknowledge Prof. D. A. Mitchell (University of Illinois at Urbana-Champaign) for providing an authentic sample of plantazolicin A and advice on purification, Peter Grice and Duncan Howe for assistance with NMR spectroscopy, and generous funding from the Royal Society (Newton International Fellowship—Z.E.W.), the German Academic Exchange Service DAAD (S.F.), and the Engineering and Physical Sciences Research Council.
External DOI: https://doi.org/10.1002/anie.201410063
This record's URL: https://www.repository.cam.ac.uk/handle/1810/246619
Attribution 2.0 UK: England & Wales
Licence URL: http://creativecommons.org/licenses/by/2.0/uk/