Tandem radical cyclization-oxygenation of 6-(2,2-dibromovinyl)-1-(2-deoxy-D-erythro-pent-1-enofuranosyl)-uracil: Synthesis of anomeric spiro nucleosides having arabino and ribo configurations

Nucleosides and Nucleotides

Volumn 15, Issue 1-3, 1996, Pages 97-107

  Kittaka, Atsushi ^a   Tsubaki, Yasuhiko ^a   Tanaka, Hiromichi ^a   Nakamura, Kazuo T ^a   Miyasaka, Tadashi ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

8 BROMO 6,1' (ETHENO) SPONGOURIDINE; HERBICIDE; NUCLEOSIDE DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0030007303     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319608002373     Document Type: Article

References (28)

1. a) Nakajima, M.; Itoi, K.; Takamatsu, Y.; Kinoshita, T.; Okazaki, T.; Kawakubo, K.; Shindo, M.; Honma, T.; Tohjigamori, M.; Haneishi, T. J. Antibiot. 1991, 44, 293-300.
2. b) Haruyama, H.; Takayama, T.; Kinoshita, T.; Kondo, M.; Nakajima, M.; Haneishi, T. J. Chem. Soc. Perkin Trans. 1 1991, 1637-1640.
3. For the synthesis of 1 and its stereoisomers: a) Mio, S.; Ichinose, R.; Goto, K.; Sugai, S.; Sato, S. Tetrahedron 1991, 47, 2111-2120. b) Mio, S.; Shiraishi, M.; Sugai, S.; Haruyama, H.; Sato, S. Ibid. 1991, 47, 2121-2132. c) Mio, S.; Kumagawa, Y.; Sugai, S. Ibid. 1991, 47, 2133-2144. d) Mio, S.; Ueda, M.; Hamura, M.; Kitagawa, J.; Sugai, S. Ibid. 1991, 47, 2145-2154. e) Fairbanks, A. J.; Ford, P. S.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 3327-3330. f) Matsumoto, M.; Kirihara, M.; Yoshino, T.; Katoh, T.; Terashima, S. Ibid. 1993, 34, 6289-6292. g) Chemla, P. Ibid. 1993, 34, 7391-7394. h) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Ibid. 1993, 34, 6119-6122. i) Harrington, P. M.; Jung, M. E. Ibid. 1994, 35, 5145-5148. j) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517-7520.
4. For the synthesis of 1 and its stereoisomers: a) Mio, S.; Ichinose, R.; Goto, K.; Sugai, S.; Sato, S. Tetrahedron 1991, 47, 2111-2120. b) Mio, S.; Shiraishi, M.; Sugai, S.; Haruyama, H.; Sato, S. Ibid. 1991, 47, 2121-2132. c) Mio, S.; Kumagawa, Y.; Sugai, S. Ibid. 1991, 47, 2133-2144. d) Mio, S.; Ueda, M.; Hamura, M.; Kitagawa, J.; Sugai, S. Ibid. 1991, 47, 2145-2154. e) Fairbanks, A. J.; Ford, P. S.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 3327-3330. f) Matsumoto, M.; Kirihara, M.; Yoshino, T.; Katoh, T.; Terashima, S. Ibid. 1993, 34, 6289-6292. g) Chemla, P. Ibid. 1993, 34, 7391-7394. h) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Ibid. 1993, 34, 6119-6122. i) Harrington, P. M.; Jung, M. E. Ibid. 1994, 35, 5145-5148. j) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517-7520.
5. For the synthesis of 1 and its stereoisomers: a) Mio, S.; Ichinose, R.; Goto, K.; Sugai, S.; Sato, S. Tetrahedron 1991, 47, 2111-2120. b) Mio, S.; Shiraishi, M.; Sugai, S.; Haruyama, H.; Sato, S. Ibid. 1991, 47, 2121-2132. c) Mio, S.; Kumagawa, Y.; Sugai, S. Ibid. 1991, 47, 2133-2144. d) Mio, S.; Ueda, M.; Hamura, M.; Kitagawa, J.; Sugai, S. Ibid. 1991, 47, 2145-2154. e) Fairbanks, A. J.; Ford, P. S.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 3327-3330. f) Matsumoto, M.; Kirihara, M.; Yoshino, T.; Katoh, T.; Terashima, S. Ibid. 1993, 34, 6289-6292. g) Chemla, P. Ibid. 1993, 34, 7391-7394. h) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Ibid. 1993, 34, 6119-6122. i) Harrington, P. M.; Jung, M. E. Ibid. 1994, 35, 5145-5148. j) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517-7520.
6. For the synthesis of 1 and its stereoisomers: a) Mio, S.; Ichinose, R.; Goto, K.; Sugai, S.; Sato, S. Tetrahedron 1991, 47, 2111-2120. b) Mio, S.; Shiraishi, M.; Sugai, S.; Haruyama, H.; Sato, S. Ibid. 1991, 47, 2121-2132. c) Mio, S.; Kumagawa, Y.; Sugai, S. Ibid. 1991, 47, 2133-2144. d) Mio, S.; Ueda, M.; Hamura, M.; Kitagawa, J.; Sugai, S. Ibid. 1991, 47, 2145-2154. e) Fairbanks, A. J.; Ford, P. S.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 3327-3330. f) Matsumoto, M.; Kirihara, M.; Yoshino, T.; Katoh, T.; Terashima, S. Ibid. 1993, 34, 6289-6292. g) Chemla, P. Ibid. 1993, 34, 7391-7394. h) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Ibid. 1993, 34, 6119-6122. i) Harrington, P. M.; Jung, M. E. Ibid. 1994, 35, 5145-5148. j) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517-7520.
7. For the synthesis of 1 and its stereoisomers: a) Mio, S.; Ichinose, R.; Goto, K.; Sugai, S.; Sato, S. Tetrahedron 1991, 47, 2111-2120. b) Mio, S.; Shiraishi, M.; Sugai, S.; Haruyama, H.; Sato, S. Ibid. 1991, 47, 2121-2132. c) Mio, S.; Kumagawa, Y.; Sugai, S. Ibid. 1991, 47, 2133-2144. d) Mio, S.; Ueda, M.; Hamura, M.; Kitagawa, J.; Sugai, S. Ibid. 1991, 47, 2145-2154. e) Fairbanks, A. J.; Ford, P. S.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 3327-3330. f) Matsumoto, M.; Kirihara, M.; Yoshino, T.; Katoh, T.; Terashima, S. Ibid. 1993, 34, 6289-6292. g) Chemla, P. Ibid. 1993, 34, 7391-7394. h) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Ibid. 1993, 34, 6119-6122. i) Harrington, P. M.; Jung, M. E. Ibid. 1994, 35, 5145-5148. j) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517-7520.
8. For the synthesis of 1 and its stereoisomers: a) Mio, S.; Ichinose, R.; Goto, K.; Sugai, S.; Sato, S. Tetrahedron 1991, 47, 2111-2120. b) Mio, S.; Shiraishi, M.; Sugai, S.; Haruyama, H.; Sato, S. Ibid. 1991, 47, 2121-2132. c) Mio, S.; Kumagawa, Y.; Sugai, S. Ibid. 1991, 47, 2133-2144. d) Mio, S.; Ueda, M.; Hamura, M.; Kitagawa, J.; Sugai, S. Ibid. 1991, 47, 2145-2154. e) Fairbanks, A. J.; Ford, P. S.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 3327-3330. f) Matsumoto, M.; Kirihara, M.; Yoshino, T.; Katoh, T.; Terashima, S. Ibid. 1993, 34, 6289-6292. g) Chemla, P. Ibid. 1993, 34, 7391-7394. h) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Ibid. 1993, 34, 6119-6122. i) Harrington, P. M.; Jung, M. E. Ibid. 1994, 35, 5145-5148. j) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517-7520.
9. For the synthesis of 1 and its stereoisomers: a) Mio, S.; Ichinose, R.; Goto, K.; Sugai, S.; Sato, S. Tetrahedron 1991, 47, 2111-2120. b) Mio, S.; Shiraishi, M.; Sugai, S.; Haruyama, H.; Sato, S. Ibid. 1991, 47, 2121-2132. c) Mio, S.; Kumagawa, Y.; Sugai, S. Ibid. 1991, 47, 2133-2144. d) Mio, S.; Ueda, M.; Hamura, M.; Kitagawa, J.; Sugai, S. Ibid. 1991, 47, 2145-2154. e) Fairbanks, A. J.; Ford, P. S.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 3327-3330. f) Matsumoto, M.; Kirihara, M.; Yoshino, T.; Katoh, T.; Terashima, S. Ibid. 1993, 34, 6289-6292. g) Chemla, P. Ibid. 1993, 34, 7391-7394. h) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Ibid. 1993, 34, 6119-6122. i) Harrington, P. M.; Jung, M. E. Ibid. 1994, 35, 5145-5148. j) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517-7520.
10. For the synthesis of 1 and its stereoisomers: a) Mio, S.; Ichinose, R.; Goto, K.; Sugai, S.; Sato, S. Tetrahedron 1991, 47, 2111-2120. b) Mio, S.; Shiraishi, M.; Sugai, S.; Haruyama, H.; Sato, S. Ibid. 1991, 47, 2121-2132. c) Mio, S.; Kumagawa, Y.; Sugai, S. Ibid. 1991, 47, 2133-2144. d) Mio, S.; Ueda, M.; Hamura, M.; Kitagawa, J.; Sugai, S. Ibid. 1991, 47, 2145-2154. e) Fairbanks, A. J.; Ford, P. S.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 3327-3330. f) Matsumoto, M.; Kirihara, M.; Yoshino, T.; Katoh, T.; Terashima, S. Ibid. 1993, 34, 6289-6292. g) Chemla, P. Ibid. 1993, 34, 7391-7394. h) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Ibid. 1993, 34, 6119-6122. i) Harrington, P. M.; Jung, M. E. Ibid. 1994, 35, 5145-5148. j) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517-7520.
11. For the synthesis of 1 and its stereoisomers: a) Mio, S.; Ichinose, R.; Goto, K.; Sugai, S.; Sato, S. Tetrahedron 1991, 47, 2111-2120. b) Mio, S.; Shiraishi, M.; Sugai, S.; Haruyama, H.; Sato, S. Ibid. 1991, 47, 2121-2132. c) Mio, S.; Kumagawa, Y.; Sugai, S. Ibid. 1991, 47, 2133-2144. d) Mio, S.; Ueda, M.; Hamura, M.; Kitagawa, J.; Sugai, S. Ibid. 1991, 47, 2145-2154. e) Fairbanks, A. J.; Ford, P. S.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 3327-3330. f) Matsumoto, M.; Kirihara, M.; Yoshino, T.; Katoh, T.; Terashima, S. Ibid. 1993, 34, 6289-6292. g) Chemla, P. Ibid. 1993, 34, 7391-7394. h) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Ibid. 1993, 34, 6119-6122. i) Harrington, P. M.; Jung, M. E. Ibid. 1994, 35, 5145-5148. j) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517-7520.
12. For the synthesis of 1 and its stereoisomers: a) Mio, S.; Ichinose, R.; Goto, K.; Sugai, S.; Sato, S. Tetrahedron 1991, 47, 2111-2120. b) Mio, S.; Shiraishi, M.; Sugai, S.; Haruyama, H.; Sato, S. Ibid. 1991, 47, 2121-2132. c) Mio, S.; Kumagawa, Y.; Sugai, S. Ibid. 1991, 47, 2133-2144. d) Mio, S.; Ueda, M.; Hamura, M.; Kitagawa, J.; Sugai, S. Ibid. 1991, 47, 2145-2154. e) Fairbanks, A. J.; Ford, P. S.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 3327-3330. f) Matsumoto, M.; Kirihara, M.; Yoshino, T.; Katoh, T.; Terashima, S. Ibid. 1993, 34, 6289-6292. g) Chemla, P. Ibid. 1993, 34, 7391-7394. h) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Ibid. 1993, 34, 6119-6122. i) Harrington, P. M.; Jung, M. E. Ibid. 1994, 35, 5145-5148. j) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517-7520.
13. Mio, S.; Sano, H.; Shindou, M.; Honma, T.; Sugai, S. Agric. Biol. Chem. 1991, 55, 1105-1109.
14. Kittaka, A.; Tanaka, H.; Odanaka, Y.; Ohnuki, K.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem., 1994, 59, 3636-3641.
15. In addition to 6, the α-anomer [yield 6.0%, deuterium content (%) at the C-2′: β/α = 69.8/20.8] and the 6-endo cyclized product (yield 7.0%, single isomer, deuterium content at the anomeric position: 96.7%) were also isolated. The stereochemistry of the latter product about C-2′ position is not known at the present time.
16. Due to anisotropic effect of the fixed C-2 carbonyl group in 4, H-2′β appears at lower field of δ 2.78 ppm as compared to H-2′α (δ 2.46 ppm). The assignment of these protons was confirmed by the presence of an NOE correlation between H-2′α and H-4′.
17. Nakamura, E.; Inubushi, T.; Aoki, S.; Machii, D. J. Am. Chem. Soc. 1991, 113, 8980-8982.
18. NOE enhancement between OH and C-H has been used to elucidate stereochemistry of cyclic molecules. For recent examples: a) Cheng, X.-C.; Varoglu, M.; Abrell, L.; Crews, P.; Lobkovsky, E.; Clardy, J. J. Org. Chem. 1994, 59, 6344-6348. b) Arnone, A.; Bravo, P.; Frigerio, M.; Viani, F. Ibid. 1994, 59, 6448-6455.
19. NOE enhancement between OH and C-H has been used to elucidate stereochemistry of cyclic molecules. For recent examples: a) Cheng, X.-C.; Varoglu, M.; Abrell, L.; Crews, P.; Lobkovsky, E.; Clardy, J. J. Org. Chem. 1994, 59, 6344-6348. b) Arnone, A.; Bravo, P.; Frigerio, M.; Viani, F. Ibid. 1994, 59, 6448-6455.
20. Although 9 can be assumed to be a single isomer, its olefinic configuration is not known.
21. A significant amount (53.3%) of the starting material (10) was recovered.
22. Sakairi, N.; Hirao, I.; Zama, Y.; Ishido, Y. Nucleosides Nucleotides 1983, 2, 221-229.
23. 2O).
24. Hydride reduction of 1′-C-branched 2′-ketouridines has been reported to yield the ribofuranosyl product predominantly: Yoshimura, Y.; Otter, B. A.; Ueda, T.; Matsuda, A. Chem. Pharm. Bull. 1992, 40, 1761-1769.
25. 2 gave a complex mixture of products, from which only 7 was isolated in 46.6% recovery.
26. Base-catalyzed interconversion of 2′- and 3′-O-(tert-butyldimethylsilyl)ribofuranosyl nucleosides in MeOH has been reported: Jones, S. S.; Reese C. B. J. Chem. Soc. Perkin I 1979, 2762-2764.
27. The H-2′ (δ 5.34 ppm) in 15 is readily assignable, because of significant down field shift due to anisotropic effect of the base moiety (cf. H-3′: δ 4.24 ppm).
28. -3.