title: Electrocyclization of oxatrienes in the construction of structurally complex pyranopyridones.
abstract: 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.
authors.affiliation: Department of Chemistry, Laboratory of Organic Chemistry, Aristotle University of Thessaloniki, University Campus, 54124, Thessaloniki, Greece.
authors.forename: Anna D
authors.initials: AD
authors.lastname: Fotiadou
authors.forename: Alexandros L
authors.initials: AL
authors.lastname: Zografos
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000475:Alkenes; D001688:Biological Products; D006574:Heterocyclic Compounds, 2-Ring; D011714:Pyrans; D011728:Pyridones