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


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Authors

Wilson, Zoe E 
Fenner, Sabine 
Ley, Steven V 

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.

Description

Keywords

cyclization, heterocycles, natural products, peptides, total synthesis, Amino Acids, Anti-Bacterial Agents, Bacillus anthracis, Cyclization, Hydrocarbons, Fluorinated, Oligopeptides, Oxazoles, Oxidation-Reduction, Sulfur Compounds, Thiazoles

Journal Title

Angew Chem Int Ed Engl

Conference Name

Journal ISSN

1433-7851
1521-3773

Volume Title

54

Publisher

Wiley
Sponsorship
Engineering and Physical Sciences Research Council (EP/K009494/1)
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.