title: Michael addition of ortho-lithiated aryloxiranes to alpha,beta-unsaturated malonates: synthesis of tetrahydroindenofuranones.
abstract: A short and efficient synthesis of tetrahydroindenofuranones based on the Michael addition of ortho-lithiated aryloxiranes to alkylidene malonates followed by the nucleophilic oxirane ring-opening and subsequent lactonization is described. The methodology has been applied to the synthesis of a structural analogue of epipodophyllotoxins.
authors.affiliation: Dipartimento Farmaco-Chimico, Università di Bari, Consorzio Interuniversitario Nazionale Metodologie e Processi Innovativi di Sintesi, Via E.Orabona 4, I-70125 Bari, Italy.
authors.forename: Antonio
authors.initials: A
authors.lastname: Salomone
authors.forename: Vito
authors.initials: V
authors.lastname: Capriati
authors.forename: Saverio
authors.initials: S
authors.lastname: Florio
authors.forename: Renzo
authors.initials: R
authors.lastname: Luisi
mesh_terms: D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D005663:Furans; D007192:Indenes; D008314:Malonates; D009942:Organometallic Compounds; D008094:Lithium