Electrocyclization of Oxatrienes in the Construction of Structurally Complex Pyranopyridones

Application of a tandem Knoevenagel/6π-electrocyclization sequence is able to produce highly substituted pyranopyridones from moderate to high yields in a one-step reaction. High diasteroselectivity is observed in some cases and was rationalized on the basis of the thermodynamic control of the evide...

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Veröffentlicht in:	Organic letters 2012-11, Vol.14 (22), p.5664-5667
Hauptverfasser:	Fotiadou, Anna D, Zografos, Alexandros L
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemical synthesis Alkaloids - chemistry Alkenes - chemistry Biological Products - chemical synthesis Biological Products - chemistry Catalysis Combinatorial Chemistry Techniques Cyclization Heterocyclic Compounds, 2-Ring - chemical synthesis Heterocyclic Compounds, 2-Ring - chemistry Molecular Structure Pyrans - chemical synthesis Pyrans - chemistry Pyridones - chemical synthesis Pyridones - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	Application of a tandem Knoevenagel/6π-electrocyclization sequence is able to produce highly substituted pyranopyridones from moderate to high yields in a one-step reaction. High diasteroselectivity is observed in some cases and was rationalized on the basis of the thermodynamic control of the evidenced reversibility of a 6π-electrocyclization reaction. Numerous examples are provided establishing a novel entry in natural product-like structures of pyranopyridone alkaloids.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol3026457