Browse > Article

Synthesis of 4′$\alpha$-C Methyl Branched Novel Adenine and Uracil Carbocyclic Nucleosides Using Ring-Closing Metathesis  

홍준희 (조선대학교 약학대학)
Publication Information
YAKHAK HOEJI / v.47, no.5, 2003 , pp. 271-275 More about this Journal
Abstract
Easy and efficient synthetic route of novel 4'-C methyl branched carbocyclic nucleosides is described. The installation of alkyl and aryl groups at 4'-position of carbocyclic nucleosides were successfully made via sequential [3,3]-sigmatropic rearrangement and ring-closing metathesis (RCM) starting from simple ketones such as acetol. Adenine and uracil were coupled via Pd(0) catalyzed reaction, followed by desilylation to give novel compounds 13 and 14, respectively.
Keywords
antiviral agents; carbocyclic nucleosides; claisen rearrangement; ring-closing metathesis (RCM);
Citations & Related Records
연도 인용수 순위
  • Reference
1 Stereoselective synthesis of 4´-α-alkylcarbovir derivative based on an asymmetric synthesis or chemoenzymatic procedure /
[ Kato,K.;Suzuki,H.;Tanaka, .;Miyasaka,T.;Baba,M.;Yamaguchi,K.;Akita,H. ] / Chem. Pharm. Bull.   DOI
2 Synthesis of 4´-cyanothymidine and analogs as potent inhibitors of HIV /
[ Yossefyeh,R.D.;Tegg,D.;Verheyden,J.P.H.;Jones,G.H.;Moffatt,J.G. ] / Teterahedron Lett.   DOI   ScienceOn
3 Stereoselective synthesis of a novel carbocyclic nucleoside /
[ Gurjar,M.K.;Maheshwar,K. ] / J. Org. Chem.   DOI   ScienceOn
4 An efficient, general asymmetri synthesis of carbocyclic nucleosides: application of an asymmetric aldol/ring-closing metathesis strategy /
[ Crimmins,M.T.;King,B.W.;Zuercher,W.J.;Choy,A.L. ] / J. Org. Chem.   DOI   ScienceOn
5 Synthesis of 4´-C-methylnucleosides /
[ Waga,T.;Nishizaki,T.;Miyakawa,J.;Ohriu,H.;Meguro,S. ] / Biosci. Biotechnol. Biochem.   DOI   ScienceOn
6 A versatile enantioselective strategy toward L-C-nucleosides : A total synthesis of L-showdomycin /
[ Trost,B.M.;Kallander,L.S. ] / J. Org. Chem.   DOI   ScienceOn
7 Synthesis of novel 3´-C-methyl-apionucleosides: an asymmetric construction of a quaternary carbon by Claisen rearrangement /
[ Hong,J.H.;Gao,M.Y.;Choi,Y.;Cheng,Y.C.;Schinazi,R.F.;Chu,C.K. ] / Carbohydrate Res.   DOI   ScienceOn
8 Synthesis and antiviral activity of acyclic analogues of 1,5-anhydrohexitol using Mitsunobu reaction /
[ Hossain,N.;Rozenski,J.;De Clercq, E.;Herdewjn,P. ] / Tetrahedron   DOI   ScienceOn
9 L592U89, a novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity /
[ Daluge,S.M.;Good,S.S.;Faletto,M.B.;Miller,W.H.;St cair, M. H.;Boone,L.R.;Tisdale,M.;Parry,N.R.;Reardon,A.E.;Dornsife,R.E.;Averett,D.R.;Krenitsky,T.A. ] / Anti-microb. Agents Chemother
10 Synthesis of 4´-C-fluoromethylnucleosides as potential antineoplastic agents /
[ Kitano,K.;Miura,S.;Ohrui,H.;Meguro,H. ] / Tetrahedron   DOI   ScienceOn
11 New isomeric analogues of anti-HIV active azidonucleosides /
[ Jeon,G.S;Nair,V. ] / Tetrahedron   DOI   ScienceOn
12 Enantiomeric synthesis of 3´-fluoro-apionucleosides using Claisen rearrangement /
[ Hong,J.H.;Lee,K.;Choi,Y.;Chu,C.K. ] / Tetrahedron Lett.   DOI   ScienceOn
13 Synthesis and biological activity of unsaturated carbocyclic purine nucleoside analogues /
[ Haines,D.R.;Tseng,C.K.H.;Marquez,V.E. ] / J. Med. Chem.   DOI
14 Efficient synthesis of novel carbocyclic nucleosides via sequential Claisen rearrangement and ring-closing metathesis /
[ Hong,J.H.;Ko,O.H. ] / Tetrahedron Lett.   DOI   ScienceOn
15 An efficient synthesis of novel carbocyclic nucleosides with use of ring-closing metathesis from D-lactose /
[ Hong,J.H.;Shim,M.J.;Ro,B.O.;Ko,O.H. ] / J. Org. Chem.   DOI   ScienceOn
16 Synthesis of novel 3´-C-methyl-4´-thioapionucleosides via highly enantioselective elaboration of quaternary carbon by [3,3]-sigmatropic rearrangement /
[ Hong,J.H.;Cao,M.Y.;Chu,C.K. ] / Tetrahedron Lett.   DOI   ScienceOn
17 Human erythrocytic purine nucleoside phosphorylase: reaction with segar-modified nucleoside substrate /
[ Stoeckler,J.D.;Cambor,C.;Parks,R.E.Jr. ] / Biochemistry   DOI   ScienceOn