Synthetic studies directed toward the assembly of the C-glycoside fragment of the telomerase inhibitor D8646-2-6.
[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.
Kanai
Akira
A
Frontier Research Center for Genomic Drug Discovery and Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Nodashi, Chiba 278-8510, Japan.
Kamino
Tomoyuki
T
Kuramochi
Kouji
K
Kobayashi
Susumu
S
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D019098:Telomerase / Q000037:antagonists & inhibitors*
C479141:D8646-2-6; D004791:Enzyme Inhibitors; D006027:Glycosides; D019098:Telomerase