Synthesis and biological evaluation of (±)-hippolachnin and analogs

被引:14
|
作者
Winter, Nils [1 ]
Rupcic, Zeljka [2 ]
Stadler, Marc [2 ]
Trauner, Dirk [1 ,3 ]
机构
[1] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13, D-81377 Munich, Germany
[2] Helmholtz Ctr InfectionRes, Inhoffenstr 7, D-38124 Braunschweig, Germany
[3] NYU, Dept Chem, Silver Ctr, 100 Washington Sq East,Room 712, New York, NY 10003 USA
来源
JOURNAL OF ANTIBIOTICS | 2019年 / 72卷 / 06期
关键词
11-STEP TOTAL-SYNTHESIS; THIOCARBONYL YLIDES; ENAMINE REACTIONS; NEW-GENERATION; MECHANISM; CARBONYL; CYCLOADDITIONS; METABOLITES; HYDROLYSIS; REAGENTS;
D O I
10.1038/s41429-019-0176-x
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Due its unique structure and its reported potent antifungal activity, the marine polyketide hippolachnin A (1) has attracted much attention in the synthetic community. Herein, we describe the development of a concise, diversifiable and scalable synthesis of the racemic natural product, which serves as a platform for the generation of bioactive analogues. Biological testing of our synthetic material did not confirm the reported antifungal activity of hippolachnin A but unraveled moderate activity against nematodes and microbes.
引用
收藏
页码:375 / 383
页数:9
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