947770-95-8Relevant academic research and scientific papers
Total synthesis of potent antifungal marine bisoxazole natural products bengazoles A and B
Bull, James A.,Balskus, Emily P.,Horan, Richard A.J.,Langner, Martin,Ley, Steven V.
, p. 5515 - 5538 (2008/02/10)
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 oxazolcs. 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.
