Total synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomers
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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.
Healy , A R , Vinale , F , Lorito , M & Westwood , N J 2015 , ' Total synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomers ' Organic Letters , vol 17 , no. 3 , pp. 692-695 . DOI: 10.1021/ol503717r
© 2015 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
DescriptionFinancial support for this project was provided by Cancer Research UK (Grant No. C21383/A6950)
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