One-pot synthesis of azanucleosides from proline derivatives

Tetrahedron Letters

Volumn 49, Issue 3, 2008, Pages 455-458

  Boto, Alicia ^a   Hernández, Dácil ^a   Hernández, Rosendo ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

Azanucleosides; Decarboxylation; Iminium ions; Nucleoside analogues; Radical reactions

Indexed keywords

AZANUCLEOSIDE DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROXYPROLINE; IMINE; NUCLEOSIDE DERIVATIVE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DECARBOXYLATION; ONE POT SYNTHESIS; RADICAL REACTION; REACTION ANALYSIS;

EID: 37449027099     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.113     Document Type: Article

References (40)

1. Kočalka P., Pohl R., Rejman D., and Rosenberg I. Tetrahedron 62 (2006) 5763-5774 and references cited therein
2. For a review article, see:. Yokoyama M., and Momotake A. Synthesis (1999) 1541-1554
3. For recent work on the subject, see:. Burton G., Ku T.W., Carr T.J., Kiesow T., Sarisky R.T., Lin-Goerke J., Hofmann G.A., Slater M.J., Haigh D., Dhanak D., Johnson V.K., Parry N.R., and Thommes P. Bioorg. Med. Chem. Lett. 17 (2007) 1930-1933
4. Qiu X.L., and Qing F.L. J. Org. Chem. 70 (2005) 3826-3837
5. Koszytkowska-Stawinska M., and Sas W. Tetrahedron Lett. 45 (2004) 5437-5440
6. Han B., Wang Z., Jaun B., Krishnamurthy R., and Eschenmoser A. Org. Lett. 5 (2003) 2071-2074
7. Buchholz M., and Reissig H.U. Eur. J. Org. Chem. (2003) 3524-3533
8. Altmann K.H., Freier S.M., Pieles U., and Winkler T. Angew. Chem., Int. Ed. Engl. 33 (1994) 1654-1657
9. Evans G.B., Furneaux R.H., Hausler H., Larsen J.S., and Tyler P.C. J. Org. Chem. 69 (2004) 2217-2220
10. Kamath V.P., Ananth S., Bantia S., and Morris Jr. P.E. J. Med. Chem. 47 (2004) 1322-1324
11. Deng L., Scharer O.D., and Verdine G.L. J. Am. Chem. Soc. 119 (1997) 7865-7866
12. For related examples, see:. Mayer A., Häberli A., and Leumann C.J. Org. Biomol. Chem. 3 (2005) 1653-1658
13. Häberli A., and Leumann C.J. Org. Lett. 4 (2002) 3275-3278
14. Boto A., Hernández D., Hernández R., Montoya A., and Suárez E. Eur. J. Org. Chem. (2007) 325-334
15. Boto A., De León Y., Gallardo J.A., and Hernández R. Eur. J. Org. Chem. (2005) 3461-3468
16. Boto A., Hernández R., and Suárez E. J. Org. Chem. 65 (2000) 4930-4937
17. For a review, see:. Hansen S.G., and Skrydstrup T. Top. Curr. Chem. 264 (2006) 135-162
18. Although the α-acetoxy amides are usually unstable and decompose during isolation, we have been able to purify an α-acetoxyglycine derived from the fragmentation of serine derivatives:. Boto A., Gallardo J.A., Hernández D., and Hernández R. J. Org. Chem. 72 (2007) 7260-7269
19. Acetoxy acetals are also formed during the radical fragmentation of carbohydrates:. Boto A., Hernández D., Hernández R., and Suárez E. J. Org. Chem. 68 (2003) 5310-5319
20. The nucleophiles were prepared from commercial bases (5-fluorouracil, thymine, uracil, benzoylcytosine, benzotriazole, and benzyloxypurin) according to Vorbrüggen protocol:. Vorbrüggen H. Acta Biochem. Pol. 43 (1996) 25-36
21. Drew M.G.B., Gorsuch S., Gould J.H.M., and Mann J. J. Chem. Soc., Perkin Trans. 1 (1999) 969-978
22. The α-methoxypyrrolidine 13 was obtained as a diastereomer mixture (2,4-cis:2,4-trans, 1:1).
23. For examples on the generation of α-methoxy nitrogen heterocycles by electrochemical methods, see:. Shono T. Tetrahedron 40 (1984) 811-850
24. Matsumura Y., Kanda Y., Shirai K., Onomura O., and Maki T. Tetrahedron 56 (2000) 7411-7422
25. Kardassis G., Brungs P., and Steckhan E. Tetrahedron 54 (1998) 3471-3478
26. Shono T., Matsumura Y., Onomura O., and Sato M. J. Org. Chem. 53 (1988) 4118-4121
27. Nishitani T., Horikawa H., Iwasaki T., Matsumoto K., Inoue I., and Miyoshi M. J. Org. Chem. 47 (1982) 1706-1712
28. The addition of methanol improved the yields. When it was omitted, (the other conditions remaining the same) the products were isolated in lower yields (50-55%).
29. For a related example, see:. Renaud P., and Seebach D. Helv. Chim. Acta 69 (1986) 1704-1710
30. For a related acyliminium intermediate, see:. Durand J.-O., Larchevêque M., and Petit Y. Tetrahedron Lett. 39 (1998) 5743-5746
31. Boto A., Hernández R., León Y., and Suárez E. J. Org. Chem. 65 (2001) 7796-7803
32. For the synthesis of other epoxy pyrrolidines and their conversion into 3,4-disubstituted pyrrolidines, see:. Kamal A., Shaik A.A., Sandbhor M., Shaheer-Malik M., and Kaga H. Tetrahedron Lett. 45 (2004) 8057-8059
33. Davis B.G., Maughan M.A.T., Chapman T.M., Villard R., and Courtney S. Org. Lett. 4 (2002) 103-106
34. Robinson J.K., Lee V., Claridge T.D.W., Baldwin J.E., and Schofield C.J. Tetrahedron 54 (1998) 981-996
35. Schumacher D.P., and Hall S.S. J. Am. Chem. Soc. 104 (1982) 6076-6080
36. Costenaro E.R., Fontoura L.A.M., Oliveira D.F., and Correia C.R.D. Tetrahedron Lett. 42 (2001) 1599-1602
37. Kumamoto H., and Tanaka H. J. Org. Chem. 67 (2002) 3541-3547
38. Ferrero M., and Gotor V. Chem. Rev. 100 (2000) 4319-4347 and references cited therein
39. Oliveira D.F., Severino E.A., and Correia C.R.D. Tetrahedron Lett. 40 (1999) 2083-2086
40. Rassu G., Pinna L., Spanu P., Ulgheri F., and Casiraghi G. Tetrahedron Lett. 35 (1994) 4019-4022