title: Unified synthesis of tirandamycins and streptolydigins.
abstract: The asymmetric total syntheses of tirandamycins A-D and tirandalydigin as well as the synthesis of the left-hand fragment of streptolydiginone and streptolydigin from a common intermediate are described. The comprehensive approach features the highly enantio- and diastereoselective assembly of the anti,anti,syn-stereotetrad unit which relies on a cinchona alkaloid-catalyzed asymmetric Morita-Baylis-Hillman reaction.
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan. susumi@nagasaki-u.ac.jp.
authors.forename: Hikaru
authors.initials: H
authors.lastname: Yoshimura
authors.affiliation: Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan.
authors.forename: Keisuke
authors.initials: K
authors.lastname: Takahashi
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan. susumi@nagasaki-u.ac.jp.
authors.forename: Jun
authors.initials: J
authors.lastname: Ishihara
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan. susumi@nagasaki-u.ac.jp.
authors.forename: Susumi
authors.initials: S
authors.lastname: Hatakeyama
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D006865:Hydrogenation; D011760:Pyrrolidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D011760:Pyrrolidinones; C545292:tirandamycin C; C545293:tirandamycin D; C055113:tirandalydigin; C003608:tirandamycin A; C021492:tirandamycin B