Synthesis of 2'-Methyl and 4'-Hydroxy Branched Novel Carbocyclic Nucleosides

2'-메칠 및 4'-하이드록시 측쇄를 가진 새로운 카보사이클릭 뉴크레오사이드의 합성

  • Published : 2003.12.01

Abstract

This paper describes a synthetic route to novel 2'-methyl and 4'-hydroxy carbocyclic nucleosides. The methyl group was successfully installed by carbonyl addition reaction of isopropenyl magnesium bromide followed by ring-closing metathesis and the hydroxy group was directly introduced from carbohydrate chiral template "D-lactose".ose".uot;.

Keywords

References

  1. Stoeckler, J. D., Cambor, C. and Parks, R. E. Jr. : Human erythrocytic purine nucleoside phosphorylase : reaction with sugar-modified nucleoside substrate. Biochemistry 19, 102 (1980) https://doi.org/10.1021/bi00542a016
  2. Crimmins, M. T.: New development in the enantioselective synthesis of cyclopentyl carbcyclic nucleosides. Tetrahedron 54, 9229 (1998)
  3. Agrofoglio, L., Suhas, E., Farese, A., Condom, R., Challand, S. R., Earl, R. A. and Guedj, R. : Synthesis of carbocyclic nucleosides. Tetrahedron 50, 10611 (1994) https://doi.org/10.1016/S0040-4020(01)89258-9
  4. Borthwick, A. D. and Biggadike, K. : Synthesis of chiral carbocyclic nucleosides. Tetrahedron 48, 571 (1992) https://doi.org/10.1016/S0040-4020(01)88122-9
  5. Borcherding, D. R., Narayanan, S., Hasobe, M., McKee, J. G., Keller, B. T. and Borchardt, R. T. : Potential inhibitors of S-adenosylmethionine- dependent methyltransferases. II. Molecular dissections of neplanocin A as potential inhibitors of S-adenosylhomocysteine hydrolase. J. Med. Chem. 31, 1729 (1988)
  6. Marquez, V. E., Lim, M.-I., Treanor, S. P., Plowman, J., Priest, M. A., Markovac, A., Khan, M.'S., Kaskar, B. and Driscoll, J. S. : Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties. J. Med. Chem. 31, 1687 (1988)
  7. Phadtare, S., Kessel, D., Corbett, T. H., Renis, H. E., Court, B. A. and Zemlicka, J. : Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor and antiviral activity. J. Med. Chem, 34, 421 (1991)
  8. O-Yang, C., Wu, H. Y., Fraser-Smith, E. B. and Walker, K. A. M. : Synthesis of 4'-Cyanothymidine and anlogues as potent inhibitors of HIV. Tetrahedron Lett. 33, 37 (1992) https://doi.org/10.1016/S0040-4039(00)77667-2
  9. Maag, H., Rydzewski, R. M., McRoberts, M. J., Crawford-Ruth, D., Verheyden, J. P. H. and Prisbe, E. J. : Synthesis and anti-HIV activity of 4'-azido- and 4'-methoxynucleosides. J. Med. Chem. 35, 1440 (1992) https://doi.org/10.1021/jm00086a013
  10. Maag, H., Nelson, J. T., Rios Steiner, J. L. and Prisbe, E. J. : Solid-state and solution conformations of the potent HIV inhibitor, 4'-azidothymidine. J. Med. Chem. 37, 431 (1994) https://doi.org/10.1021/jm00030a001
  11. Chen, M. S., Stuttman, R. T., Papp, E., Cannon, P. D., McRoberts, M. J., Bach, C., Copeland, W. C. and Wang, T. S. F. : Selective action of 4'-azidothymidine triphosphate on reverse transcriptase of human immuno-deficiency virus type 1 and human DNA polymerase $\alpha$ and $\beta$. Biochemistry 32, 6002 (1993)
  12. Matsuda, A., Takenuki, K., Itoh, H., Sasaki, T. and Ueda, T. : Radical deoxygenation of tert-alcohols in 2'-branched-chain sugar pyrimidine nucleosides: synthesis and antileukemic activity of 2'-deoxy-2'(S)-methylcytidine. Chem. Pharm. Bull. 35, 3967 (1987)
  13. Matsuda, A., Takenuki, K., Sasaki, T. and Ueda, T. : Radical deoxygenation of tert-alcohols in 1-(2-C-alkylpentofuranosyl) pyrimidines: synthesis of (2'S)-2'-deoxy-2'-C-methylcytidine, an antileukemic nucleoside. J. Med. Chem. 34, 234 (1991)
  14. Hong, J. H., Shim, M. J., Ro, B. O. and Ko, O. H. : An efficient synthesis of novel carbocyclic nucleosides with use of ring-closing metathesis from D-lactose. J. Org. Chem. 67, 6837 (2002) https://doi.org/10.1021/jo0202536
  15. Kim, J. and Hong, J. H. : Synthesis of novel apionucleosides: a short and concise synthesis of 2-deoxyapio-L- furanosyl acetate from D-lactose. Carbohydr. Res. 338, 705 (2003)
  16. Grubbs, R. H. and Chang, S. : Recent advances in olefin metathesis and its application in organic synthesis. Tetrahedron 54, 4413 (1998)
  17. Ko, O. H. and Hong, J. H. : Efficient synthesis of novel carbocyclic nucleosides via sequential Claisen rearrangement and ring-closing metathesis. Tetrahedron Lett. 43, 6399 (2002) https://doi.org/10.1016/S0040-4039(02)01384-9
  18. Hong, J. H., Oh, C. H. and Cho, J. H. : Stereocontrolled synthesis of novel 6'($\alpha$)-hydroxy carbovir analogues. Tetrahedron 59, 6103 (2003)
  19. Gurjar, M. K. and Maheshwar, K. : Stereoselective synthesis of a novel carbocyclic nucleoside. J. Org. Chem. 66, 7552 (2001) https://doi.org/10.1021/jo010718c
  20. Crimmins, M. T., King, B. w., Zuercher, W. J. and Choy, A. L. : An efficient, general asymmetric synthesis of carbocyclic nucleosides: application of an asymmetric aldol/ring-closing metathesis strategy. J. Org. Chem. 65, 8499 (2000)