Total syntheses of linear polythiazole/oxazole plantazolicin A and its biosynthetic precursor plantazolicin B.

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 by an efficient, unified, and highly convergent route featuring dicyclizations 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.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.This is the final version. It was first published by Wiley at http://onlinelibrary.wiley.com/doi/10.1002/anie.201410063/abstrac