title: A model system for the synthesis of complanadine alkaloids by "diverted Kondrat'eva" oxazole-olefin cycloaddition.
abstract: A synthetic approach to complanadine alkaloids is described which employs a Kondrat'eva reaction to construct the pyridine rings. The viability of this approach is demonstrated by its application to a model substrate accessed from unfunctionalized decalin. The key transformation affords the desired tetracyclic architecture with unprecedented incorporation of substituents on the pyridine ring, implicating the oxazole α-hydroxy group as an active participant in the cycloadduct fragmentation process.
authors.affiliation: Department of Chemistry, University of Bath, Bath, BA2 7AY, United Kingdom.
authors.forename: Mario
authors.initials: M
authors.lastname: Uosis-Martin
authors.forename: G Dan
authors.initials: GD
authors.lastname: Pantoş
authors.forename: Mary F
authors.initials: MF
authors.lastname: Mahon
authors.forename: Simon E
authors.initials: SE
authors.lastname: Lewis
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D000475:Alkenes / Q000737:chemistry*; D061565:Cycloaddition Reaction; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry
chemical_list: D000470:Alkaloids; D000475:Alkenes; D006576:Heterocyclic Compounds, 4 or More Rings; D009281:Naphthalenes; D010080:Oxazoles; D011725:Pyridines; C550939:complanadine A; C582812:complanadine B; C517127:complanadine C; C517128:complanadine D; C557833:complanadine E; C585001:lycodine; C007229:decalin