title: Total synthesis of ent-calystegine B4 via nitro-Michael/aldol reaction.
abstract: Optically active ent-calystegine B4 was prepared in 13 steps from commercially available chiral L-dimethyl tartrate. The synthesis was achieved by the Michael addition and the aldol reaction of nitromethane to form cycloheptanone in a stereoselective manner. Reduction of the nitro group in the presence of Boc(2)O accomplished an efficient conversion to amino cycloheptanone, which readily afforded the desired ent-calystegine B4.
authors.affiliation: Department of Applied Molecular Bioscience, Graduate School of Medicine, Yamaguchi University, Ube 755-8611, Japan. ak10@yamaguchi-u.ac.jp
authors.forename: Akio
authors.initials: A
authors.lastname: Kamimura
authors.forename: Koichiro
authors.initials: K
authors.lastname: Miyazaki
authors.forename: Shuzo
authors.initials: S
authors.lastname: Suzuki
authors.forename: Shingo
authors.initials: S
authors.lastname: Ishikawa
authors.forename: Hidemitsu
authors.initials: H
authors.lastname: Uno
mesh_terms: D015394:Molecular Structure; D017672:Nitrogen Compounds / Q000737:chemistry; D009662:Nortropanes / Q000138:chemical synthesis*; D012991:Solanaceous Alkaloids / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D017672:Nitrogen Compounds; D009662:Nortropanes; D012991:Solanaceous Alkaloids; C095613:calystegine B(2)