Enantioselective Synthesis of (+)-Hippolide J and Reevaluation of Antifungal Activity

被引:7
作者
Guo, Renyu [1 ]
Beattie, Sarah R. [2 ,3 ]
Krysan, Damian J. [2 ,3 ]
Brown, M. Kevin [1 ]
机构
[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
[2] Univ Iowa, Carver Coll Med, Dept Pediat, Iowa City, IA 52242 USA
[3] Univ Iowa, Carver Coll Med, Dept Microbiol Immunol, Iowa City, IA 52242 USA
关键词
CYCLOBUTANE DERIVATIVES; ALLENOATES;
D O I
10.1021/acs.orglett.0c02979
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of the reported antifungal agent (+)-hippolide J is presented. The rapid assembly of the natural product was enabled through implementation of an enantioselective isomerization/[2 + 2]-cycloaddition sequence. Due to the simplicity of the route, >100 mg of the natural product were prepared in a single pass. Anitfungal assays of hippolide J, however, confirmed that it showed no activity against several fungal strains, contrary to the isolation report.
引用
收藏
页码:7743 / 7746
页数:4
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