Total synthesis of spiruchostatin B aided by an automated synthesizer

Total synthesis of spiruchostatin B aided by an automated synthesizer

The total synthesis of a natural product HDAC inhibitor, spiruchostatin B, was successfully achieved. A 5-step synthesis that included an asymmetric aldol reaction was carried out in an automated synthesizer to provide an (E)-(S)-3-hydroxy-7-thio-4-heptenoic acid segment that is the crucial structur...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic & biomolecular chemistry 2011-05, Vol.9 (10), p.3825-3833
Hauptverfasser: Fuse, Shinichiro, Okada, Kumiko, Iijima, Yusuke, Munakata, Asami, Machida, Kazuhiro, Takahashi, Takashi, Takagi, Motoki, Shin-ya, Kazuo, Doi, Takayuki
Format: Artikel
Sprache:eng
Schlagworte:
Automation
Biological Products - chemical synthesis
Biological Products - chemistry
Cysteine - chemistry
Depsipeptides - chemical synthesis
Depsipeptides - chemistry
Histone Deacetylase Inhibitors - chemical synthesis
Histone Deacetylase Inhibitors - chemistry
Hydroxy Acids - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The total synthesis of a natural product HDAC inhibitor, spiruchostatin B, was successfully achieved. A 5-step synthesis that included an asymmetric aldol reaction was carried out in an automated synthesizer to provide an (E)-(S)-3-hydroxy-7-thio-4-heptenoic acid segment that is the crucial structure of cysteine-containing, depsipeptidic natural products such as spiruchostatins, FK228, FR901375, and largazole for their inhibitory activity against HDACs.
ISSN:1477-0520
1477-0539
DOI:10.1039/c0ob01169j