Oh, CH Hong, JH 2024-01-21T06:39:01Z 2024-01-21T06:39:01Z 2021-09-04 2004-08 0365-6233 https://pubs.kist.re.kr/handle/201004/137375 In this study, a series of 2',4-' or 3',4'-doubly branched carbocyclic nucleosides (11, 12, 19, and 20) were synthesized from simple acyclic ketone derivatives as starting materials. The installation of the 4'-quaternary carbon needed was carried out using a [3,3]-sigmatropic rearrangement. In addition, the introduction of a methyl group in the 2'- or 3'-position was accomplished by either Grignard reaction or Horner-Wadsworth-Emmons reaction with triethyl-2-phosphonopropionate, respectively. Bis-vinyl was successfully cyclized using a Grubbs' catalyst II. The natural bases (adenine, cytosine) were coupled efficiently using a Pd(O) catalyst. Although all the synthesized compounds were assayed against several viruses, only the cytosine analogue 20 showed moderate antiviral activity against the human cytomegalovirus. English WILEY-V C H VERLAG GMBH HUMAN-IMMUNODEFICIENCY-VIRUS HEPATITIS-B-VIRUS S-ADENOSYLHOMOCYSTEINE EFFICIENT SYNTHESIS CLOSING METATHESIS REPLICATION ANALOGS Synthesis and antiviral activities of novel 2 ',4 '- or 3 ',4 '-doubly branched carbocyclic nucleosides as potential antiviral agents Article 10.1002/ardp.200400875 1 ARCHIV DER PHARMAZIE, v.337, no.8, pp.457 - 463 ARCHIV DER PHARMAZIE 337 8 457 463 scie scopus 000223437900006 2-s2.0-4544348663 Chemistry, Medicinal Chemistry, Multidisciplinary Pharmacology & Pharmacy Pharmacology & Pharmacy Chemistry Article HUMAN-IMMUNODEFICIENCY-VIRUS HEPATITIS-B-VIRUS S-ADENOSYLHOMOCYSTEINE EFFICIENT SYNTHESIS CLOSING METATHESIS REPLICATION ANALOGS carbocyclic nucleosides [3,3]-sigmatropic rearrangement Horner-Wadsworth-Emmons reaction antiviral agents