title: Preparation of amino-substituted indenes and 1,4-dihydronaphthalenes using a one-pot multireaction approach: total synthesis of oxybenzo[c]phenanthridine alkaloids.
abstract: Allylic trichloroacetimidates bearing a 2-vinyl or 2-allylaryl group have been designed as substrates for a one-pot, two-step multi-bond-forming process leading to the general preparation of aminoindenes and amino-substituted 1,4-dihydronaphthalenes. The synthetic utility of the privileged structures formed from this one-pot process was demonstrated with the total synthesis of four oxybenzo[c]phenanthridine alkaloids, oxychelerythrine, oxysanguinarine, oxynitidine, and oxyavicine. An intramolecular biaryl Heck coupling reaction, catalyzed using the Hermann-Beller palladacycle was used to effect the key step during the synthesis of the natural products.
authors: WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow , Glasgow G12 8QQ, United Kingdom.
authors: Ewen D D
authors: ED
authors: Calder
authors: Fiona I
authors: FI
authors: McGonagle
authors: Alexander H
authors: AH
authors: Harkiss
authors: Grant A
authors: GA
authors: McGonagle
authors: Andrew
authors: A
authors: Sutherland
mesh_terms: D000081:Acetamides / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D000081:Acetamides; D000470:Alkaloids; D001688:Biological Products; D007192:Indenes; D009281:Naphthalenes; D010617:Phenanthridines; D014753:Vinyl Compounds; C511013:oxyavicine; C511014:oxysanguinarine; C511015:oxynitidine