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Total synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomers

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healy2015organiclett692.pdf (1.341Mb)
Date
06/02/2015
Author
Healy, A.R.
Vinale, F.
Lorito, M.
Westwood, Nicholas James
Keywords
QD Chemistry
DAS
Metadata
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Abstract
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.
Citation
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 . https://doi.org/10.1021/ol503717r
Publication
Organic Letters
Status
Peer reviewed
DOI
https://doi.org/10.1021/ol503717r
ISSN
1523-7060
Type
Journal article
Rights
© 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.
Description
Financial support for this project was provided by Cancer Research UK (Grant No. C21383/A6950)
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/6207

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