title: Synthesis of the 1-phenethyltetrahydroisoquinoline alkaloids (+)-dysoxyline, (+)-colchiethanamine, and (+)-colchiethine.
abstract: Asymmetric total syntheses of the 1-phenethyl-1,2,3,4-tetrahydroisoquinoline alkaloids (+)-dysoxyline (1), (+)-colchiethanamine (2), and (+)-colchiethine (3) are described. In the synthetic routes, coupling of a key, enatiomerically pure 1-(sulfonylmethyl)tetrahydroisoquinoline with aromatic aldehydes, performed by using the Julia-Kocienski reaction, afforded the corresponding 1-(β-styryl)-substituted tetrahydroisoquinolines with complete retention of the absolute configuration at the C1 carbon atom. Functionalization of the products generated in these processes by using four- or five-step sequences gave the target alkaloids 1-3.
authors.affiliation: Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan.
authors.forename: Raju Jannapu
authors.initials: RJ
authors.lastname: Reddy
authors.forename: Nobuyuki
authors.initials: N
authors.lastname: Kawai
authors.forename: Jun'ichi
authors.initials: J
authors.lastname: Uenishi
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D000475:Alkenes; D007546:Isoquinolines; C581337:colchiethanamine; C581339:colchiethine; C581338:dysoxyline; C039109:isoquinoline