A new entry to carbocyclic nucleosides: oxidative coupling reaction of cycloalkenylsilanes with a nucleobase mediated by hypervalent iodine reagent.
A novel method for synthesizing carbocyclic nucleosides was developed. The new synthesis includes a direct coupling reaction of cycloalkenylsilanes with a silylated nucleobase catalyzed by a hypervalent iodine reagent. By applying the method, a novel carbocyclic cytidine derivative having bis(hydroxymethyl)cyclohexene as a pseudosugar moiety, designed as a potential anti-HIV agent, was successfully synthesized.
Yoshimura
Yuichi
Y
Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan. yoshimura@tohoku-pharm.ac.jp
Ohta
Masatoshi
M
Imahori
Tatsushi
T
Imamichi
Tomozumi
T
Takahata
Hiroki
H
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003562:Cytidine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D011687:Purines / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D019380:Anti-HIV Agents; D007202:Indicators and Reagents; D009705:Nucleosides; D011687:Purines; D011743:Pyrimidines; D012821:Silanes; D003562:Cytidine; D007455:Iodine