Synthesis of the central portion of cycloviracin

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9541-9545

  Velarde, Steve ^a   Urbina, James ^a   Peña, Michael R ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; CYCLOVIRACIN B1; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030446402     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961623r     Document Type: Article

References (30)

1. Tsunakawa, M.; Komiyama, N.; Tenmyo, O.; Tomita, K.; Kawano, K.; Kotake, C.; Konishi, M.; Oki, T. J. Antibiot. 1992, 45, 1467-1471.
2. Tsunakawa, M.; Kotake, C.; Yamasaki, T.; Moriyama, T.; Komishi, M.; Oki, T. J. Antibiot. 1992, 45, 1472-1480.
3. For an example of crown ethers: Lein, G. M.; Cram, D. J. J. Am. Chem. Soc. 1985, 107, 448-455. McDaniel, C. W.; Bradshaw, J. S.; Izath, R. M. Heterocycles 1990, 30, 665-706. Aza-crown ethers: Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929-972. Aza-crown ethers incorporating a carbohydrate: Bako, P.; Fenichel, L.; Toke, L.; Davison, B. E. J. Chem. Soc., Perkin Trans. 1 1989, 2514-2516.
4. For an example of crown ethers: Lein, G. M.; Cram, D. J. J. Am. Chem. Soc. 1985, 107, 448-455. McDaniel, C. W.; Bradshaw, J. S.; Izath, R. M. Heterocycles 1990, 30, 665-706. Aza-crown ethers: Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929-972. Aza-crown ethers incorporating a carbohydrate: Bako, P.; Fenichel, L.; Toke, L.; Davison, B. E. J. Chem. Soc., Perkin Trans. 1 1989, 2514-2516.
5. For an example of crown ethers: Lein, G. M.; Cram, D. J. J. Am. Chem. Soc. 1985, 107, 448-455. McDaniel, C. W.; Bradshaw, J. S.; Izath, R. M. Heterocycles 1990, 30, 665-706. Aza-crown ethers: Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929-972. Aza-crown ethers incorporating a carbohydrate: Bako, P.; Fenichel, L.; Toke, L.; Davison, B. E. J. Chem. Soc., Perkin Trans. 1 1989, 2514-2516.
6. For an example of crown ethers: Lein, G. M.; Cram, D. J. J. Am. Chem. Soc. 1985, 107, 448-455. McDaniel, C. W.; Bradshaw, J. S.; Izath, R. M. Heterocycles 1990, 30, 665-706. Aza-crown ethers: Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929-972. Aza-crown ethers incorporating a carbohydrate: Bako, P.; Fenichel, L.; Toke, L.; Davison, B. E. J. Chem. Soc., Perkin Trans. 1 1989, 2514-2516.
7. Therisod, M.; Klibanov, A. M. J. Am. Chem. Soc. 1986, 108, 5638-5640. Therisod, M.; Klibanov, A. M. J. Am. Chem. Soc. 1987, 109, 3977-3981. Riva, S.; Chopineau, J.; Kieboom, A. P. G.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 584-589.
8. Therisod, M.; Klibanov, A. M. J. Am. Chem. Soc. 1986, 108, 5638-5640. Therisod, M.; Klibanov, A. M. J. Am. Chem. Soc. 1987, 109, 3977-3981. Riva, S.; Chopineau, J.; Kieboom, A. P. G.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 584-589.
9. Therisod, M.; Klibanov, A. M. J. Am. Chem. Soc. 1986, 108, 5638-5640. Therisod, M.; Klibanov, A. M. J. Am. Chem. Soc. 1987, 109, 3977-3981. Riva, S.; Chopineau, J.; Kieboom, A. P. G.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 584-589.
10. Seebach, D.; Sutter, M. A.; Weber, R. H.; Züger, M. F. Org. Synth. 1984, 63, 1-9. Nakamura, K.; Kawai, Y.; Oka, S.; Ohno, A. Bull. Chem. Soc. Jpn. 1989, 62, 875-879. Crump, D. R. Aust. J. Chem. 1982, 35, 1945-1948.
11. Seebach, D.; Sutter, M. A.; Weber, R. H.; Züger, M. F. Org. Synth. 1984, 63, 1-9. Nakamura, K.; Kawai, Y.; Oka, S.; Ohno, A. Bull. Chem. Soc. Jpn. 1989, 62, 875-879. Crump, D. R. Aust. J. Chem. 1982, 35, 1945-1948.
12. Seebach, D.; Sutter, M. A.; Weber, R. H.; Züger, M. F. Org. Synth. 1984, 63, 1-9. Nakamura, K.; Kawai, Y.; Oka, S.; Ohno, A. Bull. Chem. Soc. Jpn. 1989, 62, 875-879. Crump, D. R. Aust. J. Chem. 1982, 35, 1945-1948.
13. Keck, G. E.; Murry, J. A. J. Org. Chem. 1991, 56, 6606-6611. Noyori, R.; Ohkuma, T.; Kitamura, M.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856-5858.
14. Keck, G. E.; Murry, J. A. J. Org. Chem. 1991, 56, 6606-6611. Noyori, R.; Ohkuma, T.; Kitamura, M.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856-5858.
15. 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. Bonner, W. A. J. Am. Chem. Soc. 1951, 73, 3126-3132.
16. 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. Bonner, W. A. J. Am. Chem. Soc. 1951, 73, 3126-3132.
17. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519. König, W. A.; Nippe, K.-S.; Mischnick, P. Tetrahedron Lett. 1990, 31, 6867-6868.
18. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519. König, W. A.; Nippe, K.-S.; Mischnick, P. Tetrahedron Lett. 1990, 31, 6867-6868.
19. Sakaki, J.-i.; Kobayashi, S.; Sato, M.; Kaneko, C. Chem Pharm. Bull. 1989, 37, 2952-2960.
20. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235. Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155-173. Mori, K.; Qian, Z.-H. Leibigs Ann. Chem. 1994, 291-295. Kunz, H.; Harreus, A. Liebigs Ann. Chem. 1982, 41-48. Collins, P.; Ferner, R. Monosaccharides - Their Chemistry and Their Roles in Natural Products; Wiley: New York, 1995; pp 60-184.
21. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235. Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155-173. Mori, K.; Qian, Z.-H. Leibigs Ann. Chem. 1994, 291-295. Kunz, H.; Harreus, A. Liebigs Ann. Chem. 1982, 41-48. Collins, P.; Ferner, R. Monosaccharides - Their Chemistry and Their Roles in Natural Products; Wiley: New York, 1995; pp 60-184.
22. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235. Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155-173. Mori, K.; Qian, Z.-H. Leibigs Ann. Chem. 1994, 291-295. Kunz, H.; Harreus, A. Liebigs Ann. Chem. 1982, 41-48. Collins, P.; Ferner, R. Monosaccharides - Their Chemistry and Their Roles in Natural Products; Wiley: New York, 1995; pp 60-184.
23. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235. Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155-173. Mori, K.; Qian, Z.-H. Leibigs Ann. Chem. 1994, 291-295. Kunz, H.; Harreus, A. Liebigs Ann. Chem. 1982, 41-48. Collins, P.; Ferner, R. Monosaccharides - Their Chemistry and Their Roles in Natural Products; Wiley: New York, 1995; pp 60-184.
24. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235. Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155-173. Mori, K.; Qian, Z.-H. Leibigs Ann. Chem. 1994, 291-295. Kunz, H.; Harreus, A. Liebigs Ann. Chem. 1982, 41-48. Collins, P.; Ferner, R. Monosaccharides - Their Chemistry and Their Roles in Natural Products; Wiley: New York, 1995; pp 60-184.
25. Nakajima, N.; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139-4142.
26. Hanessian, S.; Lavalee, P. Can. J. Chem. 1975, 53, 2975-2977. Franke, F.; Guthrie, R. D. Aust. J. Chem. 1977, 639-647.
27. Hanessian, S.; Lavalee, P. Can. J. Chem. 1975, 53, 2975-2977. Franke, F.; Guthrie, R. D. Aust. J. Chem. 1977, 639-647.
28. Kucumoto, S.; K. Sakai, K.; Shiba, T. Bull. Chem. Soc. Jpn. 1986, 59, 1296-1298. Goel, O. P.; Seamans, R. E. Synthesis 1973, 538-539.
29. Kucumoto, S.; K. Sakai, K.; Shiba, T. Bull. Chem. Soc. Jpn. 1986, 59, 1296-1298. Goel, O. P.; Seamans, R. E. Synthesis 1973, 538-539.
30. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamuguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.