Total Synthesis and Biological Evaluation of the Tetramic Acid Based Natural Product Harzianic Acid and Its Stereoisomers

被引：26
|
作者：
Healy, Alan R. [1 ,2 ]
Vinale, Francesco [3 ]
Lorito, Matteo [3 ,4 ]
Westwood, Nicholas J. [1 ,2 ]
机构：
[1] Univ St Andrews, Sch Chem & Biomed Sci Res Complex, St Andrews KY16 9ST, Fife, Scotland
[2] EaStCHEM, St Andrews KY16 9ST, Fife, Scotland
[3] CNR, IPSP, I-80055 Portici, Italy
[4] Univ Napoli Federico II, Dipartimento Agr, I-80138 Portici, Italy
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 03期
关键词：
TRICHODERMA; INHIBITOR;
D O I：
10.1021/ol503717r
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The bioactive natural product harzianic acid was prepared for the first time in just six steps (longest linear sequence) with an overall yield of 22%. The identification of conditions to telescope amide bond formation and a Lacey-Dieckmann reaction into one pot proved important. The three stereoisomers of harzianic acid were also prepared, providing material for comparison of their biological activity. While all of the isomers promoted root growth, improved antifungal activity was unexpectedly associated with isomers in the enantiomeric series opposite that of harzianic acid.
引用
收藏
页码：692 / 695
页数：4
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