title: Short asymmetric synthesis of phenanthroindolizidines through chiral homoallylic sulfinamines.
abstract: An efficient stereocontrolled preparation of chiral phenanthroindolizidines is detailed. The synthesis relies on the stereoselective indium-mediated allylation of 2-(phenanthren-9-yl)acetaldehyde derivatives with chiral tert-butylsulfinamide. Chemoselective transformations from the corresponding homoallylic sulfinamine allow the synthesis of the phenanthroindolizidines in only three synthetic operations, without any detectable racemization. Following this procedure, the synthesis of natural (-)-tylophorine was successfully accomplished.
authors: 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: Cintia
authors: C
authors: Anton-Torrecillas
authors: Jose C
authors: JC
authors: Gonzalez-Gomez
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010616:Phenanthrenes / Q000138:chemical synthesis / Q000737:chemistry; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D000498:Allyl Compounds; D000588:Amines; D007212:Indolizines; D010616:Phenanthrenes; D010618:Phenanthrolines; D013452:Sulfonium Compounds; C521640:phenanthroindolizidine; C004218:tylophorine