Synthesis of spirocyclic C-arylribosides via cyclotrimerization.
[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.
Yamamoto
Yoshihiko
Y
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
Hashimoto
Toru
T
Hattori
Kozo
K
Kikuchi
Makoto
M
Nishiyama
Hisao
H
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
D000480:Alkynes; D053280:Diynes; D007783:Lactones; D013141:Spiro Compounds; D012266:Ribose; D008094:Lithium