Cargando…
Total synthesis of biselide A
A total synthesis of the marine macrolide biselide A is described that relies on an enantiomerically enriched α-chloroaldehyde as the sole chiral building block. Several strategies to construct the macrocycle are presented including a macrocyclic Reformatsky reaction that ultimately provides access...
Autores principales: | , , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179649/ https://www.ncbi.nlm.nih.gov/pubmed/34168790 http://dx.doi.org/10.1039/d0sc06223e |
_version_ | 1783703830011052032 |
---|---|
author | Challa, Venugopal Rao Kwon, Daniel Taron, Matthew Fan, Hope Kang, Baldip Wilson, Darryl Haeckl, F. P. Jake Keerthisinghe, Sandra Linington, Roger G. Britton, Robert |
author_facet | Challa, Venugopal Rao Kwon, Daniel Taron, Matthew Fan, Hope Kang, Baldip Wilson, Darryl Haeckl, F. P. Jake Keerthisinghe, Sandra Linington, Roger G. Britton, Robert |
author_sort | Challa, Venugopal Rao |
collection | PubMed |
description | A total synthesis of the marine macrolide biselide A is described that relies on an enantiomerically enriched α-chloroaldehyde as the sole chiral building block. Several strategies to construct the macrocycle are presented including a macrocyclic Reformatsky reaction that ultimately provides access to the natural product in a longest linear sequence of 18 steps. Biological testing of synthetic biselide A suggests this macrolide disrupts cell division through a mechanism related to the regulation of microtubule cytoskeleton organization. Overall, this concise synthesis and insight gained into the mechanism of action should inspire medicinal chemistry efforts directed at structurally related anticancer marine macrolides. |
format | Online Article Text |
id | pubmed-8179649 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81796492021-06-23 Total synthesis of biselide A Challa, Venugopal Rao Kwon, Daniel Taron, Matthew Fan, Hope Kang, Baldip Wilson, Darryl Haeckl, F. P. Jake Keerthisinghe, Sandra Linington, Roger G. Britton, Robert Chem Sci Chemistry A total synthesis of the marine macrolide biselide A is described that relies on an enantiomerically enriched α-chloroaldehyde as the sole chiral building block. Several strategies to construct the macrocycle are presented including a macrocyclic Reformatsky reaction that ultimately provides access to the natural product in a longest linear sequence of 18 steps. Biological testing of synthetic biselide A suggests this macrolide disrupts cell division through a mechanism related to the regulation of microtubule cytoskeleton organization. Overall, this concise synthesis and insight gained into the mechanism of action should inspire medicinal chemistry efforts directed at structurally related anticancer marine macrolides. The Royal Society of Chemistry 2021-03-12 /pmc/articles/PMC8179649/ /pubmed/34168790 http://dx.doi.org/10.1039/d0sc06223e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Challa, Venugopal Rao Kwon, Daniel Taron, Matthew Fan, Hope Kang, Baldip Wilson, Darryl Haeckl, F. P. Jake Keerthisinghe, Sandra Linington, Roger G. Britton, Robert Total synthesis of biselide A |
title | Total synthesis of biselide A |
title_full | Total synthesis of biselide A |
title_fullStr | Total synthesis of biselide A |
title_full_unstemmed | Total synthesis of biselide A |
title_short | Total synthesis of biselide A |
title_sort | total synthesis of biselide a |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179649/ https://www.ncbi.nlm.nih.gov/pubmed/34168790 http://dx.doi.org/10.1039/d0sc06223e |
work_keys_str_mv | AT challavenugopalrao totalsynthesisofbiselidea AT kwondaniel totalsynthesisofbiselidea AT taronmatthew totalsynthesisofbiselidea AT fanhope totalsynthesisofbiselidea AT kangbaldip totalsynthesisofbiselidea AT wilsondarryl totalsynthesisofbiselidea AT haecklfpjake totalsynthesisofbiselidea AT keerthisinghesandra totalsynthesisofbiselidea AT liningtonrogerg totalsynthesisofbiselidea AT brittonrobert totalsynthesisofbiselidea |