A radical cyclization approach to the formal total syntheses of platencin

Two different strategies leading to formal total syntheses of platencin are described. The first strategy involving Claisen rearrangement and radical cyclization provides a rapid access to the core structure of platencin, and also use minimum protective-group operations. The second strategy, a prote...

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Veröffentlicht in:	Organic & biomolecular chemistry 2011-10, Vol.9 (22), p.7877-7886
Hauptverfasser:	Palanichamy, Kalanidhi, Subrahmanyam, Ayyagari V, Kaliappan, Krishna P
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetyltransferases - antagonists & inhibitors Acetyltransferases - metabolism Aminophenols - analysis Aminophenols - chemical synthesis Aminophenols - pharmacology Anti-Bacterial Agents - analysis Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - pharmacology Bacteria - drug effects Bacteria - enzymology Bacterial Infections - drug therapy Bacterial Infections - microbiology Chemistry, Pharmaceutical - methods Cyclization Drug Discovery Escherichia coli Proteins - antagonists & inhibitors Escherichia coli Proteins - metabolism Fatty Acid Synthase, Type II - antagonists & inhibitors Fatty Acid Synthase, Type II - metabolism Fatty Acids - metabolism Free Radicals - chemistry Humans Lipid Metabolism - drug effects Molecular Structure Polycyclic Compounds - analysis Polycyclic Compounds - chemical synthesis Polycyclic Compounds - pharmacology Stereoisomerism
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Zusammenfassung:	Two different strategies leading to formal total syntheses of platencin are described. The first strategy involving Claisen rearrangement and radical cyclization provides a rapid access to the core structure of platencin, and also use minimum protective-group operations. The second strategy, a protecting group-free route, utilizes a 6-exo-trig radical cyclization and aldol condensation as key steps leading to the formal synthesis of platencin.
ISSN:	1477-0520 1477-0539
DOI:	10.1039/c1ob06155k