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Total Syntheses of Linear Polythiazole/Oxazole Plantazolicin A and Its Biosynthetic Precursor Plantazolicin B
Author(s) -
Wilson Zoe E.,
Fenner Sabine,
Ley Steven V.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201410063
Subject(s) - oxazole , total synthesis , natural product , chemistry , stereochemistry , combinatorial chemistry , convergent synthesis
Abstract 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.