Gephyronic Acid, a Missing Link between Polyketide Inhibitors of Eukaryotic Protein Synthesis (Part II): Total Synthesis of Gephyronic Acid

19 steps in the longest linear sequence are required in the 27 step total synthesis of gephyronic acid. A key step is a diastereodifferentiating Mukaiyama aldol reaction of an aldehyde and an enolsilane (see picture, PG: protecting group). The strongly cytotoxic target compound is a structural relat...

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Veröffentlicht in:	Angewandte Chemie (International ed.) 2011-01, Vol.50 (4), p.942-945
Hauptverfasser:	Anderl, Timo, Nicolas, Lionel, Münkemer, Johanna, Baro, Angelika, Sasse, Florenz, Steinmetz, Heinrich, Jansen, Rolf, Höfle, Gerhard, Taylor, Richard E, Laschat, Sabine
Format:	Artikel
Sprache:	eng
Schlagworte:	aldol reaction Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Fatty Acids, Monounsaturated - chemical synthesis Fatty Acids, Monounsaturated - chemistry Fatty Acids, Monounsaturated - pharmacology Molecular Structure Myxococcales - chemistry natural products Polyketide Synthases - antagonists & inhibitors Polyketide Synthases - metabolism polyketides Protein Biosynthesis - drug effects Stereoisomerism stereoselectivity Structure-Activity Relationship total synthesis
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Zusammenfassung:	19 steps in the longest linear sequence are required in the 27 step total synthesis of gephyronic acid. A key step is a diastereodifferentiating Mukaiyama aldol reaction of an aldehyde and an enolsilane (see picture, PG: protecting group). The strongly cytotoxic target compound is a structural relative of the polyketide tedanolide and was isolated from the myxobacterium Archangium gephyra.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201005605