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

A.R. Healy; F. Vinale; M. Lorito; Nicholas James Westwood

doi:10.1021/ol503717r

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

A.R. Healy, F. Vinale, M. Lorito, Nicholas James Westwood

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	692-695
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	3
Early online date	28 Jan 2015
DOIs	https://doi.org/10.1021/ol503717r
Publication status	Published - 6 Feb 2015

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10.1021/ol503717r

healy2015organiclett692
© 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.
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The Cambridge Crystallographic Data Centre - deposition number 1034467
Healy, A. (Creator), Izumikawa, M. (Creator), Slawin, A. M. Z. (Creator), Shin-ya, K. (Creator) & Westwood, N. J. (Creator), Cambridge Crystallographic Data Centre, 2015
https://dx.doi.org/10.5517/cc13qfx5
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title = "Total synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomers",

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.",

author = "A.R. Healy and F. Vinale and M. Lorito and Westwood, {Nicholas James}",

note = "Financial support for this project was provided by Cancer Research UK (Grant No. C21383/A6950) ",

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T1 - Total synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomers

AU - Healy, A.R.

AU - Vinale, F.

AU - Lorito, M.

AU - Westwood, Nicholas James

N1 - Financial support for this project was provided by Cancer Research UK (Grant No. C21383/A6950)

PY - 2015/2/6

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N2 - 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.

AB - 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.

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DO - 10.1021/ol503717r

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SP - 692

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JF - Organic Letters

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

Abstract

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The Cambridge Crystallographic Data Centre - deposition number 1034467

Cite this