The Total Synthesis of the Bioactive Natural Product Plantazolicin A and Its Biosynthetic Precursor Plantazolicin B.
Chemistry (Weinheim an Der Bergstrasse, Germany)
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Fenner, S., Wilson, Z., & Ley, S. (2016). The Total Synthesis of the Bioactive Natural Product Plantazolicin A and Its Biosynthetic Precursor Plantazolicin B.. Chemistry (Weinheim an Der Bergstrasse, Germany), 22 15902-15912. https://doi.org/10.1002/chem.201603157
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.
German Academic Exchange Service DAAD, Royal Society (Newton International Fellowship), Engineering and Physical Sciences Research Council (grants EP/ K009494/1 and EP/K039520/1)
External DOI: https://doi.org/10.1002/chem.201603157
This record's URL: https://www.repository.cam.ac.uk/handle/1810/260224