A new entry to carbocyclic nucleosides: oxidative coupling reaction of cycloalkenylsilanes with a nucleobase mediated by hypervalent iodine reagent

Yuichi Yoshimura; Masatoshi Ohta; Tatsushi Imahori; Tomozumi Imamichi; Hiroki Takahata

doi:10.1021/ol8012155

A new entry to carbocyclic nucleosides: oxidative coupling reaction of cycloalkenylsilanes with a nucleobase mediated by hypervalent iodine reagent

Org Lett. 2008 Aug 21;10(16):3449-52. doi: 10.1021/ol8012155. Epub 2008 Jul 10.

Authors

Yuichi Yoshimura¹, Masatoshi Ohta, Tatsushi Imahori, Tomozumi Imamichi, Hiroki Takahata

Affiliation

¹ Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan. yoshimura@tohoku-pharm.ac.jp

PMID: 18613695
DOI: 10.1021/ol8012155

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-HIV Agents / chemical synthesis*
Anti-HIV Agents / chemistry
Cytidine / analogs & derivatives
Cytidine / chemical synthesis*
Cytidine / chemistry
Indicators and Reagents / chemistry*
Iodine / chemistry*
Molecular Structure
Nucleosides / chemical synthesis*
Nucleosides / chemistry
Oxidation-Reduction
Purines / chemistry
Pyrimidines / chemistry
Silanes / chemistry*
Stereoisomerism

Substances

Anti-HIV Agents
Indicators and Reagents
Nucleosides
Purines
Pyrimidines
Silanes
Cytidine
Iodine