title: Concise asymmetric syntheses of novel phenanthroquinolizidines.
abstract: The first preparation of enantioenriched phenanthroquinolizidines with a quaternary center at C14a was accomplished in seven steps from readily available starting materials. Key steps were an efficient dynamic kinetic allylation of a diastereomeric mixture of chiral tert-butylsulfinyl ketimines and the construction of a piperidine E ring by rhodium catalyzed hydroformylation. The Stevens rearrangement of the corresponding N-benzyl derivatives took place smoothly, allowing the installation of a benzyl moiety at C9 in a trans relationship with the methyl group. The cytoxicity of the prepared phenanthroquinolizidines was evaluated against different human cancer cell lines.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain. josecarlos.gonzalez@ua.es.
authors.forename: Cintia
authors.initials: C
authors.lastname: Anton-Torrecillas
authors.forename: María Isabel
authors.initials: MI
authors.lastname: Loza
authors.forename: José
authors.initials: J
authors.lastname: Brea
authors.forename: Jose C
authors.initials: JC
authors.lastname: Gonzalez-Gomez
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D002384:Catalysis; D045744:Cell Line, Tumor; D005260:Female; D006801:Humans; D020128:Inhibitory Concentration 50; D008297:Male; D015394:Molecular Structure; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D010618:Phenanthrolines; D011807:Quinolizines; C521641:phenanthroquinolizidine; D012238:Rhodium