Synthesis of anomeric spiro uracil nucleosides with an orthoester structure: Stereoselective cyclization controlled by the C6-substituent

Tetrahedron Letters

Volumn 38, Issue 36, 1997, Pages 6421-6424

  Kittaka, Atsushi ^a   Tanaka, Hiromichi ^a   Kato, Hajime ^a   Nonaka, Yumiko ^a   Nakamura, Kazuo T ^a   Miyasaka, Tadashi ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE; SPIRO COMPOUND; URACIL DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0030845986     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01486-X     Document Type: Article

References (30)

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2. For reviews, see: a) Pratviel, G.; Bernadou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746-769. b) Nicolaou, K. C.; Dai, W.-M. ibid. 1991, 30, 1387-1416.
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8. c) a leading reference to form spiroketals, but in the 5-exo-trig mode, see: Brown, C. D. S.; Simpkins, N. S.; Clinch, K. Tetrahedron Lett. 1993, 34, 131-132.
9. For syntheses of anomeric spiro nucleosides, see: a) Kittaka, A.; Tanaka, H.; Odanaka, Y.; Ohnuki, K.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1994, 59, 3636-3641. b) Kittaka, A.; Tsubaki, Y.; Tanaka, H.; Nakamura, K. T.; Miyasaka, T. Nucleosides Nucleotides 1996, 15, 97-107. c) Kittaka, A.; Yamada, N.; Tanaka, H.; Nakamura, K. T.; Miyasaka, T. Nucleosides Nucleotides 1996, 15, 1447-1457. d) Yoshimura, Y.; Otter, B. A.; Ueda, T.; Matsuda, A. Chem. Pharm. Bull 1992, 40, 1761-1769. e) Sarma, M. S. P.; Megati, S.; Klein, R. S.; Otter, B. A. Nucleosides Nucleotides 1995, 14, 393-396.
10. For syntheses of anomeric spiro nucleosides, see: a) Kittaka, A.; Tanaka, H.; Odanaka, Y.; Ohnuki, K.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1994, 59, 3636-3641. b) Kittaka, A.; Tsubaki, Y.; Tanaka, H.; Nakamura, K. T.; Miyasaka, T. Nucleosides Nucleotides 1996, 15, 97-107. c) Kittaka, A.; Yamada, N.; Tanaka, H.; Nakamura, K. T.; Miyasaka, T. Nucleosides Nucleotides 1996, 15, 1447-1457. d) Yoshimura, Y.; Otter, B. A.; Ueda, T.; Matsuda, A. Chem. Pharm. Bull 1992, 40, 1761-1769. e) Sarma, M. S. P.; Megati, S.; Klein, R. S.; Otter, B. A. Nucleosides Nucleotides 1995, 14, 393-396.
11. For syntheses of anomeric spiro nucleosides, see: a) Kittaka, A.; Tanaka, H.; Odanaka, Y.; Ohnuki, K.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1994, 59, 3636-3641. b) Kittaka, A.; Tsubaki, Y.; Tanaka, H.; Nakamura, K. T.; Miyasaka, T. Nucleosides Nucleotides 1996, 15, 97-107. c) Kittaka, A.; Yamada, N.; Tanaka, H.; Nakamura, K. T.; Miyasaka, T. Nucleosides Nucleotides 1996, 15, 1447-1457. d) Yoshimura, Y.; Otter, B. A.; Ueda, T.; Matsuda, A. Chem. Pharm. Bull 1992, 40, 1761-1769. e) Sarma, M. S. P.; Megati, S.; Klein, R. S.; Otter, B. A. Nucleosides Nucleotides 1995, 14, 393-396.
12. For syntheses of anomeric spiro nucleosides, see: a) Kittaka, A.; Tanaka, H.; Odanaka, Y.; Ohnuki, K.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1994, 59, 3636-3641. b) Kittaka, A.; Tsubaki, Y.; Tanaka, H.; Nakamura, K. T.; Miyasaka, T. Nucleosides Nucleotides 1996, 15, 97-107. c) Kittaka, A.; Yamada, N.; Tanaka, H.; Nakamura, K. T.; Miyasaka, T. Nucleosides Nucleotides 1996, 15, 1447-1457. d) Yoshimura, Y.; Otter, B. A.; Ueda, T.; Matsuda, A. Chem. Pharm. Bull 1992, 40, 1761-1769. e) Sarma, M. S. P.; Megati, S.; Klein, R. S.; Otter, B. A. Nucleosides Nucleotides 1995, 14, 393-396.
13. For syntheses of anomeric spiro nucleosides, see: a) Kittaka, A.; Tanaka, H.; Odanaka, Y.; Ohnuki, K.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1994, 59, 3636-3641. b) Kittaka, A.; Tsubaki, Y.; Tanaka, H.; Nakamura, K. T.; Miyasaka, T. Nucleosides Nucleotides 1996, 15, 97-107. c) Kittaka, A.; Yamada, N.; Tanaka, H.; Nakamura, K. T.; Miyasaka, T. Nucleosides Nucleotides 1996, 15, 1447-1457. d) Yoshimura, Y.; Otter, B. A.; Ueda, T.; Matsuda, A. Chem. Pharm. Bull 1992, 40, 1761-1769. e) Sarma, M. S. P.; Megati, S.; Klein, R. S.; Otter, B. A. Nucleosides Nucleotides 1995, 14, 393-396.
14. a) Ames, B. N. Science 1983, 221, 1256-1264.
15. b) Ide, H.; Yamaoka, T.; Kimura, Y. Biochemistry 1994, 33, 7127-7133.
16. Glycosidic spiro orthoesters have been synthesized based on homolysis of the anomeric C-H bond: Praly, J.-P.; Boyé, S.; Joseph, B.; Rollin, P. Tetrahedron Lett. 1993, 34, 3419-3420.
17. a) For a recent review, see: Majetich, G.; Wheless, K. Tetrahedron, 1995, 51, 7095-7129. b) For leading references, see: Heusler, K.; Kalvoda, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 525-538. Kalvoda, J.; Heusler, K. Synthesis 1971, 501-526. c) For leading usage of DIB, see: Martín, A.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1996, 61, 3999-4006.
18. a) For a recent review, see: Majetich, G.; Wheless, K. Tetrahedron, 1995, 51, 7095-7129. b) For leading references, see: Heusler, K.; Kalvoda, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 525-538. Kalvoda, J.; Heusler, K. Synthesis 1971, 501-526. c) For leading usage of DIB, see: Martín, A.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1996, 61, 3999-4006.
19. a) For a recent review, see: Majetich, G.; Wheless, K. Tetrahedron, 1995, 51, 7095-7129. b) For leading references, see: Heusler, K.; Kalvoda, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 525-538. Kalvoda, J.; Heusler, K. Synthesis 1971, 501-526. c) For leading usage of DIB, see: Martín, A.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1996, 61, 3999-4006.
20. a) For a recent review, see: Majetich, G.; Wheless, K. Tetrahedron, 1995, 51, 7095-7129. b) For leading references, see: Heusler, K.; Kalvoda, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 525-538. Kalvoda, J.; Heusler, K. Synthesis 1971, 501-526. c) For leading usage of DIB, see: Martín, A.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1996, 61, 3999-4006.
21. a) Tanaka, H.; Hayakawa, H.; lijima, S.; Haraguchi, K.; Miyasaka, T. Tetrahedron 1985, 41, 861-866.
22. b) Tanaka, H.; Hayakawa, H.; Miyasaka, T. Tetrahedron 1982, 38, 2635-2642. The secondary alcohols 6a and 6b were separated by HPLC (hexane-EtOAc=1/1).
23. Experimental details of the X-ray structure determination, ORTEP representations and tables of fractional atomic coordinates, thermal parameters, interatomic distances and angles for 2b, 7α and 11β were deposited by the editor at the Cambridge Crystallographic Data Center.
24. For convenience, the α-spiro nucleosides refer to the compounds in which the base moiety occupies the opposite face to the 4′-hydroxymethyl group.
25. 1H NMR, FAB Mass, elemental analysis, UV).
26. hi this system, the O8 atom can take only two possible envelope conformations for a 5-memberd ring puckering, i.e. over or below the plane. For anomeric effect of the spiro ketal system, see: Deslongchamps P. Stereo electronic Effects in Organic Chemistry, Pergamon Press: Oxford, 1983; pp 4-53.
27. 9) It is also clear that pro-S hydrogen undergoes quasi 1,3-diaxial interaction with the O4′ atom in this case.
28. a) Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370-2374.
29. b) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakizawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
30. 2 (1:9)/20 min, and 80% AcOH/rt/2.5 h.