title: Polycyclic compounds by Ugi-Pictet-Spengler sequence.
abstract: A general approach to architecturally stimulating polycyclic structures is described by a concise, two-step procedure including a Ugi MCR (multicomponent reaction) and a subsequent Pictet-Spengler reaction starting from phenylethylamine-derived isocyanides. Ten compounds are described in full experimental detail, and yields range from medium to very good. Some of the reactions run with a high degree of stereoselectivity. The compound structures resemble steroid hormones and alkaloid classes of natural products. Exemplary products have been fully reduced to their tertiary amines. As such they could potentially become interesting biological probes.
authors.affiliation: Drug Discovery Institute, University of Pittsburgh, Biomedical Science Tower 3, 3501 Fifth Avenue, Pittsburgh, Pennsylvania 15261, United States.
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.forename: Sarah
authors.initials: S
authors.lastname: Ollio
authors.forename: Eberhardt
authors.initials: E
authors.lastname: Herdtweck
authors.forename: Alexander
authors.initials: A
authors.lastname: Dömling
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010627:Phenethylamines / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000588:Amines; D001688:Biological Products; D003486:Cyanides; D010627:Phenethylamines; D011083:Polycyclic Compounds