A new route to famciclovir via palladium catalysed allylation

Tetrahedron

Volumn 56, Issue 26, 2000, Pages 4589-4595

  Freer, Richard ^a   Geen, Graham R ^a   Ramsay, Thomas W ^a   Share, Andrew C ^a   Slater, Graham R ^a   Smith, Neil M ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Allylation; Purine; Rearrangement

Indexed keywords

1,3 DIOXANE DERIVATIVE; ALLYL COMPOUND; CARBONIC ACID; FAMCICLOVIR; PALLADIUM; PURINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034705359     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00373-2     Document Type: Article

References (31)

1. (a) Harnden, M. R. Drugs of the Future 1989, 14, 347-358.
2. (b) Marquez, V. E.; Lim, M.-I. Med. Res. Rev. 1986, 6, 1-40.
3. (c) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571-623.
4. (d) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670.
5. Trost B.M., Madsen R., Guile S.G., Elia A.E.H. Angew. Chem. Int. Ed. Engl. 35:1996;1569-1572.
6. Trost B.M., Li L., Guile S.D. J. Am. Chem. Soc. 114:1992;8745-8747.
7. Merlo V., Reece F.J., Roberts S.M., Gregson M., Storer R. J. Chem. Soc. Perkin Trans. 1. 1993;1717-1718.
8. Harnden M.R., Jarvest R.L., Boyd M.R., Sutton D., Vere Hodge R.A. J. Med. Chem. 32:1989;1738-1743.
9. (a) Geen, G. R.; Grinter, T. J.; Kincey, P. M.; Jarvest, R. L. Tetrahedron 1990, 46, 6903-6914.
10. (b) Choudary, B. M.; Geen, G. R.; Kincey, P. M.; Parratt, M. J.; Dales, J. R. M.; Johnson, G. P.; O'Donnell, S.; Tudor, D. W.; Woods, J. R. M.; Nucleosides, Nucleotides 1996, 15, 981-994.
11. (c) Geen, G. R.; Kincey, P. M.; Choudary, B. M. Tetrahedron Lett. 1992, 33, 4609-4612.
12. (d) Hijiya, T.; Yamashita, K.; Kojima, M.; Uchida, Y.; Katayama, S.; Torii, T.; Shiragami, H.; Izawa, K. Nucleosides, Nucleotides 1999, 18, 653-654.
13. (e) Brand, B.; Reese, C. B.; Soug, Q.; Visintin, C. Tetrahedron 1999, 55, 5239-5252.
14. Kjellberg J., Johansson N.G. Nucleosides, Nucleotides. 8:1989;225-256.
15. (a) Dudycz, L. W.; Wright, G. E. Nucleosides, Nucleotides 1984, 3, 33-44.
16. (b) Vorbrüggen, H.; Höfle, G. Chem. Ber. 1981, 114, 1256-1268.
17. (a) Baker, B. R.; Tanna, P. M. J. Org. Chem. 1965, 30, 2857-2858.
18. (b) Lira, E. P.; Huffman, C. W. J. Org. Chem. 1966, 31, 2188-2191.
19. Gundersen L.-L., Benneche T., Rise F., Gogoll A., Undheim K. Acta. Chem. Scand. 46:1992;761-771.
20. Trost B.M., Kuo G.-H., Benneche T. J. Am. Chem. Soc. 110:1988;621-622.
21. Haines D.R., Tseng C.K.H., Marquez V.E. J. Med. Chem. 30:1987;943-947.
22. Murahashi S.-I., Taniguchi Y., Imada Y., Tanigawa Y. J. Org. Chem. 54:1989;3292-3303.
23. Hoppe D., Schminke H., Kleemann H.-W. Tetrahedron. 45:1989;687-694.
24. 13C NMR spectra which were in agreement with published data for N-9 and N-7 alkylated purines. See Kjellberg, J.; Johansson, N. G. Tetrahedron 1986, 42, 6541-6544.
25. 3 and dppe under the conditions described in Experimental for the analogous conversion of 19 to 18.
26. Amatore, C.; Broeker, G.; Jutand, A.; Khalil, F. J. Am. Chem. Soc. 1997, 119, 5176-5185.
27. (b) It is possible that oxidative addition to 18 occurs to regenerate 20 although no evidence has been obtained to support this.
28. Lecture bottles purchased from the Aldrich Chemical Company containing mixtures of 1000 ppm oxygen or carbon monoxide in argon were used to provide the inert atmosphere for these experiments.
29. Tsuji J. Tetrahedron. 42:1986;4361-4401.
30. 1H NMR analysis of reaction mixtures. For a literature precedent catalysed by rhodium; see Frauenrath, H.; Kaulard, M. Synlett 1994, 517-518.
31. Selective reduction of the alkene without the concomitant hydrogenolysis of the 6-chloro group was achieved by hydrogenation in the absence of triethylamine. Isolation of 2,2-dimethyl-5-[2-(2-amino-6-chloropurin-9-yl)]ethyl-1,3-dioxane by this approach represents a formal synthesis of the N9-substituted guanine acyclonucleoside, penciclovir (see Harnden, M. R.; Jarvest, R. L. Tetrahedron Lett. 1985, 26, 4265-4268).