Michael addition of ortho-lithiated aryloxiranes to alpha,beta-unsaturated malonates: synthesis of tetrahydroindenofuranones.
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.
Salomone
Antonio
A
Dipartimento Farmaco-Chimico, Università di Bari, Consorzio Interuniversitario Nazionale Metodologie e Processi Innovativi di Sintesi, Via E.Orabona 4, I-70125 Bari, Italy.
Capriati
Vito
V
Florio
Saverio
S
Luisi
Renzo
R
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
D004852:Epoxy Compounds; D005663:Furans; D007192:Indenes; D008314:Malonates; D009942:Organometallic Compounds; D008094:Lithium