title: The synthesis of isoquinoline alkaloid and its related compounds using alanine derivatives as chiral auxiliaries.
abstract: Chiral 1-substituted isoquinoline derivatives, which were obtained by the reaction using alanine derivatives as chiral auxiliaries, were transformed to (S)-2,3,9,10,11-pentamethoxyhomoprotoberberine (7) and a synthetic intermediate for O-methylkreysigine (9) in good yields and high stereoselectivity. The corresponding chiral allyl derivative of isoquinoline was transformed to a pyrrolidinoisoquinoline (16) in a highly enantioselective manner.
authors.affiliation: School of Pharmaceutical Sciences, Showa University, Tokyo, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Itoh
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Nagata
authors.forename: Masashi
authors.initials: M
authors.lastname: Yokoya
authors.forename: Michiko
authors.initials: M
authors.lastname: Miyazaki
authors.forename: Keiko
authors.initials: K
authors.lastname: Kameoka
authors.forename: Shigeru
authors.initials: S
authors.lastname: Nakamura
authors.forename: Akio
authors.initials: A
authors.lastname: Ohsawa
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D000470:Alkaloids / Q000138:chemical synthesis*; D007546:Isoquinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013678:Technology, Pharmaceutical / Q000379:methods
chemical_list: D000470:Alkaloids; D007546:Isoquinolines; D000409:Alanine