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Yamamoto, Y. et al.

Yamamoto, Hashimoto, Hattori, Kikuchi, Nishiyama,

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.[1]

References

Synthesis of spirocyclic C-arylribosides via cyclotrimerization. Yamamoto, Y., Hashimoto, T., Hattori, K., Kikuchi, M., Nishiyama, H. Org. Lett. (2006) [Pubmed]

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