title: Synthesis of spirocyclic C-arylribosides via cyclotrimerization.
abstract: [reaction: see text] Spirocyclic C-arylribosides were synthesized from the known gamma-ribonolactone derivative. Lithium acetylide addition followed by glycosylation with 3-(trimethylsilyl)propargyl alcohol converted the ribonolactone to silylated diynes. After desilylation or iodination, subsequent ruthenium-catalyzed cycloaddition of resultant diynes with alkynes or chloroacetonitrile gave spirocyclic C-arylribosides.
authors.affiliation: Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552, Japan. omyy@apc.titech.ac.jp
authors.forename: Yoshihiko
authors.initials: Y
authors.lastname: Yamamoto
authors.forename: Toru
authors.initials: T
authors.lastname: Hashimoto
authors.forename: Kozo
authors.initials: K
authors.lastname: Hattori
authors.forename: Makoto
authors.initials: M
authors.lastname: Kikuchi
authors.forename: Hisao
authors.initials: H
authors.lastname: Nishiyama
mesh_terms: D000480:Alkynes / Q000737:chemistry; D003500:Cyclization; D053280:Diynes / Q000737:chemistry; D006031:Glycosylation; D007783:Lactones / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D012266:Ribose / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D053280:Diynes; D007783:Lactones; D013141:Spiro Compounds; D012266:Ribose; D008094:Lithium