Synthesis and anti-HCMV activity of novel 2',3', 4'-trimethyl branched carbocyclic nucleosides.
This article reports the synthesis of novel 2',3',4'-trimethyl branched carbocyclic nucleosides. The introduction of a methyl group in the 2' and 3'-position was accomplished by sequential Horner-Wadsworth-Emmons reaction and isopropenyl magnesiumbromide addition, respectively. The construction of the 4'-quaternary carbon needed was carried out using a [3,3]-sigmatropic rearrangement. Bis-vinyls were successfully cyclized using a Grubbs catalyst II. The natural bases (adenine, cytosine) were efficiently coupled with the use of a Pd(O) catalyst.
Kim
Aihong
A
College of Pharmacy, Chosun University, Kwangiu, Republic of Korea.
Hong
Joon Hee
JH
D043383:Adenosylhomocysteinase / Q000037:antagonists & inhibitors*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000378:metabolism; D001555:Benzene Derivatives / Q000138:chemical synthesis*; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D012333:RNA, Messenger / Q000378:metabolism*
D000998:Antiviral Agents; D001555:Benzene Derivatives; D009705:Nucleosides; D012333:RNA, Messenger; D043383:Adenosylhomocysteinase