Synthetic studies directed toward the assembly of the C-glycoside fragment of the telomerase inhibitor D8646-2-6

Akira Kanai; Tomoyuki Kamino; Kouji Kuramochi; Susumu Kobayashi

doi:10.1021/ol034873k

Synthetic studies directed toward the assembly of the C-glycoside fragment of the telomerase inhibitor D8646-2-6

Org Lett. 2003 Aug 7;5(16):2837-9. doi: 10.1021/ol034873k.

Authors

Akira Kanai¹, Tomoyuki Kamino, Kouji Kuramochi, Susumu Kobayashi

Affiliation

¹ Frontier Research Center for Genomic Drug Discovery and Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Nodashi, Chiba 278-8510, Japan.

PMID: 12889887
DOI: 10.1021/ol034873k

Abstract

[reaction: see text] Construction and characterization of the C-glycosidic moiety of telomerase inhibitor D8646-2-6 (1) are described. This is the first example of the C-glycosylation using electron-poor aromatics, 4-hydroxypyrone, as a glycosyl acceptor. The glycosylation reaction and base-promoted isomerization affords desired beta-C-glycoside in a 61% overall yield.

MeSH terms

Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Glycosides / chemical synthesis*
Glycosides / chemistry*
Telomerase / antagonists & inhibitors*

Substances

D8646-2-6
Enzyme Inhibitors
Glycosides
Telomerase