title: Enantioselective synthesis of SB-203207.
abstract: Total synthesis of SB-203207 (1) was achieved, beginning with a desymmetrical C-H insertion reaction of a diazoester bearing our recently developed chiral auxiliary. Utilizing the optically active bicyclo[3.3.0]octane ring, four stereogenic centers were efficiently constructed in sequence. Finally, mild oxidation of 27 to carboxylic acid via a cyanohydrin intermediate and hydrolysis of cyanide to carboxyamide in the presence of the labile enamide group completed an efficient total synthesis of 1.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka and Global COE Program , 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors.forename: Yasuo
authors.initials: Y
authors.lastname: Hirooka
authors.forename: Kazutada
authors.initials: K
authors.lastname: Ikeuchi
authors.forename: Yuichiro
authors.initials: Y
authors.lastname: Kawamoto
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Akao
authors.forename: Takumi
authors.initials: T
authors.lastname: Furuta
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Asakawa
authors.forename: Makoto
authors.initials: M
authors.lastname: Inai
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Wakimoto
authors.forename: Tohru
authors.initials: T
authors.lastname: Fukuyama
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Kan
mesh_terms: D002384:Catalysis; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007192:Indenes; C410786:SB 203207; D013449:Sulfonamides