YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

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

Ring-Closing Metathesis 반응을 이용한 새로운 4-메칠 아데닌 및 유라실 카보사이클릭 뉴크레오사이드의 합성

  • Published : 2003.10.01
Download PDF
⟨ Previous Next ⟩

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

References

  1. Biochemistry v.19 Human erythrocytic purine nucleoside phosphorylase: reaction with segar-modified nucleoside substrate Stoeckler,J.D.;Cambor,C.;Parks,R.E.Jr. https://doi.org/10.1021/bi00542a016
  2. Anti-microb. Agents Chemother v.41 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.
  3. Tetrahedron v.53 Synthesis of 4´-C-fluoromethylnucleosides as potential antineoplastic agents Kitano,K.;Miura,S.;Ohrui,H.;Meguro,H. https://doi.org/10.1016/S0040-4020(97)00844-2
  4. Teterahedron Lett. v.33 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. https://doi.org/10.1016/S0040-4039(00)77667-2
  5. Biosci. Biotechnol. Biochem. v.57 Synthesis of 4´-C-methylnucleosides Waga,T.;Nishizaki,T.;Miyakawa,J.;Ohriu,H.;Meguro,S. https://doi.org/10.1271/bbb.57.1433
  6. Tetrahedron Lett. v.43 Efficient synthesis of novel carbocyclic nucleosides via sequential Claisen rearrangement and ring-closing metathesis Hong,J.H.;Ko,O.H. https://doi.org/10.1016/S0040-4039(02)01384-9
  7. Carbohydrate Res. v.328 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. https://doi.org/10.1016/S0008-6215(00)00005-7
  8. Tetrahedron Lett. v.40 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. https://doi.org/10.1016/S0040-4039(98)02324-7
  9. Tetrahedron Lett. v.39 Enantiomeric synthesis of 3´-fluoro-apionucleosides using Claisen rearrangement Hong,J.H.;Lee,K.;Choi,Y.;Chu,C.K. https://doi.org/10.1016/S0040-4039(98)00567-X
  10. J. Org. Chem. v.67 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. https://doi.org/10.1021/jo025984k
  11. J. Org. Chem. v.66 Stereoselective synthesis of a novel carbocyclic nucleoside Gurjar,M.K.;Maheshwar,K. https://doi.org/10.1021/jo010718c
  12. J. Org. Chem. v.65 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. https://doi.org/10.1021/jo005535p
  13. J. Org. Chem. v.64 A versatile enantioselective strategy toward L-C-nucleosides : A total synthesis of L-showdomycin Trost,B.M.;Kallander,L.S. https://doi.org/10.1021/jo990195x
  14. J. Med. Chem. v.30 Synthesis and biological activity of unsaturated carbocyclic purine nucleoside analogues Haines,D.R.;Tseng,C.K.H.;Marquez,V.E. https://doi.org/10.1021/jm00388a036
  15. Tetrahedron v.52 Synthesis and antiviral activity of acyclic analogues of 1,5-anhydrohexitol using Mitsunobu reaction Hossain,N.;Rozenski,J.;De Clercq, E.;Herdewjn,P. https://doi.org/10.1016/0040-4020(96)00818-6
  16. Tetrahedron v.52 New isomeric analogues of anti-HIV active azidonucleosides Jeon,G.S;Nair,V. https://doi.org/10.1016/0040-4020(96)00766-1
  17. Chem. Pharm. Bull. v.47 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. https://doi.org/10.1248/cpb.47.1256