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

[Image: see text] 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. Th...

Descripción completa

Detalles Bibliográficos
Autores principales: Healy, Alan R., Vinale, Francesco, Lorito, Matteo, Westwood, Nicholas J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4737532/
https://www.ncbi.nlm.nih.gov/pubmed/25629709
http://dx.doi.org/10.1021/ol503717r
_version_ 1782413493555691520
author Healy, Alan R.
Vinale, Francesco
Lorito, Matteo
Westwood, Nicholas J.
author_facet Healy, Alan R.
Vinale, Francesco
Lorito, Matteo
Westwood, Nicholas J.
author_sort Healy, Alan R.
collection PubMed
description [Image: see text] 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.
format Online
Article
Text
id pubmed-4737532
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-47375322016-02-10 Total Synthesis and Biological Evaluation of the Tetramic Acid Based Natural Product Harzianic Acid and Its Stereoisomers Healy, Alan R. Vinale, Francesco Lorito, Matteo Westwood, Nicholas J. Org Lett [Image: see text] 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. American Chemical Society 2015-01-28 2015-02-06 /pmc/articles/PMC4737532/ /pubmed/25629709 http://dx.doi.org/10.1021/ol503717r Text en Copyright © 2015 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Healy, Alan R.
Vinale, Francesco
Lorito, Matteo
Westwood, Nicholas J.
Total Synthesis and Biological Evaluation of the Tetramic Acid Based Natural Product Harzianic Acid and Its Stereoisomers
title Total Synthesis and Biological Evaluation of the Tetramic Acid Based Natural Product Harzianic Acid and Its Stereoisomers
title_full Total Synthesis and Biological Evaluation of the Tetramic Acid Based Natural Product Harzianic Acid and Its Stereoisomers
title_fullStr Total Synthesis and Biological Evaluation of the Tetramic Acid Based Natural Product Harzianic Acid and Its Stereoisomers
title_full_unstemmed Total Synthesis and Biological Evaluation of the Tetramic Acid Based Natural Product Harzianic Acid and Its Stereoisomers
title_short Total Synthesis and Biological Evaluation of the Tetramic Acid Based Natural Product Harzianic Acid and Its Stereoisomers
title_sort total synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4737532/
https://www.ncbi.nlm.nih.gov/pubmed/25629709
http://dx.doi.org/10.1021/ol503717r
work_keys_str_mv AT healyalanr totalsynthesisandbiologicalevaluationofthetetramicacidbasednaturalproductharzianicacidanditsstereoisomers
AT vinalefrancesco totalsynthesisandbiologicalevaluationofthetetramicacidbasednaturalproductharzianicacidanditsstereoisomers
AT loritomatteo totalsynthesisandbiologicalevaluationofthetetramicacidbasednaturalproductharzianicacidanditsstereoisomers
AT westwoodnicholasj totalsynthesisandbiologicalevaluationofthetetramicacidbasednaturalproductharzianicacidanditsstereoisomers

Ejemplares similares