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  • Title: Total synthesis of potent antifungal marine bisoxazole natural products bengazoles A and B.
    Author: Bull JA, Balskus EP, Horan RA, Langner M, Ley SV.
    Journal: Chemistry; 2007; 13(19):5515-38. PubMed ID: 17440905.
    Abstract:
    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.
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