Total syntheses of linear polythiazole/oxazole plantazolicin A and its biosynthetic precursor plantazolicin B.
Change log
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
1521-3773
Volume Title
54
Publisher
Wiley
Publisher DOI
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.