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The Total Synthesis of the Bioactive Natural Product Plantazolicin A and Its Biosynthetic Precursor Plantazolicin B.

Accepted version
Peer-reviewed

Type

Article

Change log

Authors

Fenner, Sabine 

Abstract

Herein, we describe our full investigations into the synthesis of the peptide-derived natural product plantazolicin A, a compound that demonstrates promising selective activity against the causative agent of anthrax toxicity, and its biosynthetic precursor plantazolicin B. This report particularly focuses on the challenging preparation of the arginine containing thiazole fragment, including the development of a robust, high yielding procedure that avoids the use of sulfurating agents. Extensive studies on the design of a coherent protecting group strategy and the establishment of a step-efficient dicyclization/oxidation approach allowed high levels of convergence for the construction of the oxazole fragments. This has led to a unified, highly convergent synthesis for both plantazolicin A and B.

Description

Keywords

antibiotics, heterocycles, natural products, polyazole, total synthesis, Biological Products, Oligopeptides, Oxazoles, Oxidation-Reduction, Thiazoles

Journal Title

Chemistry

Conference Name

Journal ISSN

0947-6539
1521-3765

Volume Title

22

Publisher

Wiley
Sponsorship
Engineering and Physical Sciences Research Council (EP/K009494/1)
Engineering and Physical Sciences Research Council (EP/K039520/1)
German Academic Exchange Service DAAD, Royal Society (Newton International Fellowship), Engineering and Physical Sciences Research Council (grants EP/ K009494/1 and EP/K039520/1)