114. Aza-claisen rearrangement: Synthesis of 5'-branched 5'- aminothymidines

Helvetica Chimica Acta

Volumn 80, Issue 5, 1997, Pages 1589-1606

  Ammenn, Jochen ^a,b   Altmann, Karl Heinz ^a,c   Belluš, Daniel ^a,d  

^a CIBA GEIGY LTD   (Switzerland)

^b TFL   (Germany)

^c NOVARTIS PHARMA AG   (Switzerland)

^d UNIVERSITY OF FREIBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

NIKKOMYCIN; THYMIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DNA STRAND BREAKAGE; DRUG STABILITY; DRUG SYNTHESIS; GENE REARRANGEMENT; GENETIC LINKAGE; NONHUMAN; RNA BINDING; X RAY ANALYSIS;

EID: 0030788964     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.19970800517     Document Type: Article

References (31)

1. 'Nucleosides and Nucleotides as Antitumor and Antiviral Agents', Eds. C. K. Chu and D. C. Baker, Plenum, New York, 1993;
2. P. Alexander, A. Holý, Collect. Czech. Chem. Commun. 1994, 59, 2127.
3. For a recent review on the synthesis of complex nucleoside antibiotics, see S. Knapp, Chem. Rev. 1995, 95, 1859.
4. For recent general reviews on antisense oligonucleotides, see S. T. Crooke, Med. Res. Rev. 1996, 16, 319;
5. J. F. Milligan, M. D. Matteucci, J. C. Martin, J. Med. Chem. 1993, 36, 1923.
6. For recent reviews on chemically modifed oligonucleotides, see A. De Mesmaeker, R. Häner, P. Martin, H. E. Moser, Acc. Chem. Res. 1995, 28, 366;
7. A. De Mesmaeker, K.-H. Altmann, A. Waldner, S. Wendeborn, Curr. Opinion Struct. Biol. 1995, 343;
8. M. D. Matteucci, Persp. Drug Discov. Des. 1996, 4, 1.
9. J. Wang, P. J. Middleton, Tetrahedron Lett. 1996, 37, 2739;
10. A. S. Saha, T. J. Caulfield, C. Hobbs, D. A. Upson, C. Waychunas, A. M. Yawman, J. Org. Chem. 1995, 60, 788.
11. A. De Mesmaeker, Synlett, submitted.
12. P. Garner, L. M. Park, Tetrahedron Lett. 1989, 30, 5065.
13. a) A. Dondoni, F. Junquera, F. L. Merchan, P. Merino, T. Tejero, Tetrahedron Lett. 1994, 35, 9439;
14. b) A. Chen, I. Savage, E. J. Thomas, P. D. Wilson, Tetrahedron Lett., ibid. 1993, 34, 6769;
15. c) A. G. M. Barrett, S. A. Lebold, J. Org. Chem. 1990, 33, 3853.
16. C. M. Evina, G. Guillerm, Tetrahedron Lett. 1996, 37, 163.
17. T. Mukaiyama, K. Suzuki, T. Yamada, F. Tabusa, Tetrahedron 1990, 46, 265.
18. N. Chida, K. Koizumu, Y. Kitada, C. Yokoyama, S. Ogawa, J. Chem. Soc., Chem. Commun. 1994, 111.
19. Y. Auberson, P. Vogel, Tetrahedron 1990, 46, 7019.
20. For general reviews, see L. E. Overman, Angew. Chem. Int. Ed. 1984, 23, 579;
21. L. E. Overman, Acc. Chem. Res. 1980, 13, 218.
22. a) J. Gonda, A.-C. Helland, B. Ernst, D. Belluš, Synthesis 1993, 729;
23. b) P. L. Armstrong, I. C. Coull, A. T. Hewson, M. J. Slater, Tetrahedron Lett. 1995, 36, 4311;
24. c) H. Imogaï, Y. Petit, M. Larchevêque, Synlett 1997, 615.
25. K. Tandano, K. Shimada, A. Miyake, J. Ishihara, S. Ogawa, Bull. Chem. Soc. Jpn. 1989, 62, 3978.
26. H. Gilman, R. G. Jones, J. Am. Chem. Soc. 1943, 65, 1458.
27. A. M. Doherty, B. E. Kornberg, M. D. Reily, J. Org. Chem. 1993, 58, 795;
28. Y. Ichikawa, Chem. Lett. 1990, 1347.
29. F. Weygand, E. Frauendorfer, Chem. Ber. 1970, 103, 2437.
30. J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512.
31. G. Stork, C. Zhang, S. Organov, R. Schultz, Tetrahedron Lett. 1995, 36, 6387.