Total synthesis of biselide A.
Journal
Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951
Informations de publication
Date de publication:
12 Mar 2021
12 Mar 2021
Historique:
entrez:
25
6
2021
pubmed:
26
6
2021
medline:
26
6
2021
Statut:
epublish
Résumé
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.
Identifiants
pubmed: 34168790
doi: 10.1039/d0sc06223e
pii: d0sc06223e
pmc: PMC8179649
doi:
Types de publication
Journal Article
Langues
eng
Pagination
5534-5543Informations de copyright
This journal is © The Royal Society of Chemistry.
Déclaration de conflit d'intérêts
There are no conflicts to declare.
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