Synthesis of spirocyclic C-arylribosides via cyclotrimerization |
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| Authors: | Yamamoto Yoshihiko Hashimoto Toru Hattori Kozo Kikuchi Makoto Nishiyama Hisao |
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| Institution: | 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 |
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| 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. |
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