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Total Synthesis of Potent Antifungal Marine Bisoxazole Natural Products Bengazoles A and B
Author(s) -
Bull James A.,
Balskus Emily P.,
Horan Richard A. J.,
Langner Martin,
Ley Steven V.
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700033
Subject(s) - oxazole , stereocenter , total synthesis , antifungal , stereochemistry , chemistry , cycloaddition , pharmacophore , natural product , combinatorial chemistry , biology , organic chemistry , enantioselective synthesis , microbiology and biotechnology , catalysis
The bengazoles are a family of marine natural products that display potent antifungal activity and a unique structure, containing two oxazole rings flanking a single carbon atom. Total syntheses of bengazole A and B are described, which contain a sensitive stereogenic centre at this position between the two oxazoles. Additionally, the synthesis of 10‐ epi ‐bengazole A is reported. Two parallel synthetic routes were investigated, relying on construction of the 2,4‐disubstituted oxazole under mild conditions and a diastereoselective 1,3‐dipolar cycloaddition. Our successful route is high yielding, provides rapid access to single stereoisomers of the complex natural products and allows the synthesis of analogues for biological evaluation.