title: Synthesis of the core ring system of the stemona alkaloids by cascade condensation, cyclization, intramolecular cycloaddition.
abstract: Condensation of an aldehyde with an α-amino-ester, followed by a tandem process involving cyclization to a seven-membered ring, deprotonation to an intermediate azomethine ylide and intramolecular dipolar cycloaddition gave tricyclic products related to stenine and neostenine.
authors.affiliation: Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, UKS3 7HF.
authors.forename: Adam J M
authors.initials: AJ
authors.lastname: Burrell
authors.forename: Luke
authors.initials: L
authors.lastname: Watson
authors.forename: Nathaniel G
authors.initials: NG
authors.lastname: Martin
authors.forename: Niall
authors.initials: N
authors.lastname: Oram
authors.forename: Iain
authors.initials: I
authors.lastname: Coldham
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D003500:Cyclization; D041901:Stemonaceae / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000470:Alkaloids; D000588:Amines; C441784:stenine