Conjugate additions of sulfur-stabilized anions to unsaturated lactams. Synthesis of polyfunctionalized benzo[a]quinolizinone systems.
Conjugate addition reactions of sulfur-stabilized nucleophiles to the delta-lactam unit of tetrahydrobenzo[a]benzoquinolizines have been studied. The stereochemical outcome of the conjugate addition reaction depends on the nature of the substituent at the angular position, thus 2,11b-cis or 2,11b-trans diastereomers could be obtained selectively. The tandem conjugate addition-alkylation also takes place in good yields and with high diastereoselectivity. The polyfunctionalized hexahydrobenzo[a]quinolizinone systems obtained could be further elaborated toward emetine-like structures.
García
Eva
E
Departamento de Química Organica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea, Apdo. 644, 48080 Bilbao, Spain.
Lete
Esther
E
Sotomayor
Nuria
N
D000838:Anions; D002625:Chemistry, Organic / Q000379:methods*; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*
D000838:Anions; D006574:Heterocyclic Compounds, 2-Ring; D007769:Lactams; D013457:Sulfur Compounds