Synthesis of C-aryl glycosides related to the chrysomycins

Tetrahedron

Volumn 52, Issue 46, 1996, Pages 14437-14458

  Hart, David J ^a   Merriman, Gregory H ^a   Young, David G J ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHRYSOMYCIN B;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ELECTROCHEMISTRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030580415     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00876-9     Document Type: Article

References (46)

1. 1. For isolation and structure determination of the chrysomycins A and B see Strelitz, F.; Flon, H.; Asheshov, I. N. J. Bacteriol. 1955, 69, 280. Weiss, U.; Yoshihira, K.; Highet, R. J.; White, R. J.; Wei, T. T. J. Antibiotics 1982, 35, 1194. Chrysomycins A and B appear to be identical to the antibiotics virenomycin M and virenomycin V, respectively: Kulyaeva, V. V.; Kudinova, M. K.; Potapova, N. P.; Rubasheva, L. M.; Brazhnikova, N. G.; Rosynoi, B. V.; Bekker, A. R. Bioorg. Khim. 1978, 4, 1087. Chrysomycins A and B are also either identical or antipodal to the antitumor antibiotics albacarcin M and albacarcin V, respectively: Matson, J. A.; Myllymaki, R. W.; Doyle, T. W.; Bush, J. A. U. S. Patent No. 4,461,831.
2. 1. For isolation and structure determination of the chrysomycins A and B see Strelitz, F.; Flon, H.; Asheshov, I. N. J. Bacteriol. 1955, 69, 280. Weiss, U.; Yoshihira, K.; Highet, R. J.; White, R. J.; Wei, T. T. J. Antibiotics 1982, 35, 1194. Chrysomycins A and B appear to be identical to the antibiotics virenomycin M and virenomycin V, respectively: Kulyaeva, V. V.; Kudinova, M. K.; Potapova, N. P.; Rubasheva, L. M.; Brazhnikova, N. G.; Rosynoi, B. V.; Bekker, A. R. Bioorg. Khim. 1978, 4, 1087. Chrysomycins A and B are also either identical or antipodal to the antitumor antibiotics albacarcin M and albacarcin V, respectively: Matson, J. A.; Myllymaki, R. W.; Doyle, T. W.; Bush, J. A. U. S. Patent No. 4,461,831.
3. 1. For isolation and structure determination of the chrysomycins A and B see Strelitz, F.; Flon, H.; Asheshov, I. N. J. Bacteriol. 1955, 69, 280. Weiss, U.; Yoshihira, K.; Highet, R. J.; White, R. J.; Wei, T. T. J. Antibiotics 1982, 35, 1194. Chrysomycins A and B appear to be identical to the antibiotics virenomycin M and virenomycin V, respectively: Kulyaeva, V. V.; Kudinova, M. K.; Potapova, N. P.; Rubasheva, L. M.; Brazhnikova, N. G.; Rosynoi, B. V.; Bekker, A. R. Bioorg. Khim. 1978, 4, 1087. Chrysomycins A and B are also either identical or antipodal to the antitumor antibiotics albacarcin M and albacarcin V, respectively: Matson, J. A.; Myllymaki, R. W.; Doyle, T. W.; Bush, J. A. U. S. Patent No. 4,461,831.
4. 1. For isolation and structure determination of the chrysomycins A and B see Strelitz, F.; Flon, H.; Asheshov, I. N. J. Bacteriol. 1955, 69, 280. Weiss, U.; Yoshihira, K.; Highet, R. J.; White, R. J.; Wei, T. T. J. Antibiotics 1982, 35, 1194. Chrysomycins A and B appear to be identical to the antibiotics virenomycin M and virenomycin V, respectively: Kulyaeva, V. V.; Kudinova, M. K.; Potapova, N. P.; Rubasheva, L. M.; Brazhnikova, N. G.; Rosynoi, B. V.; Bekker, A. R. Bioorg. Khim. 1978, 4, 1087. Chrysomycins A and B are also either identical or antipodal to the antitumor antibiotics albacarcin M and albacarcin V, respectively: Matson, J. A.; Myllymaki, R. W.; Doyle, T. W.; Bush, J. A. U. S. Patent No. 4,461,831.
5. 2. For structurally related C-aryl glycosides see Findlay, J. A.; Liu, J.-S.; Radics, L.; Can. J. Chem. 1983, 61, 323. Sehgal, S. N.; Czerkawski, H.; Kudelski, A.; Pandev, K.; Saucier, R.; Vezina, C. J. Antibiotics 1983, 36, 355. Balitz, D. M.; O'Herron, F. A.; Bush, J.; Vyas, D. M.; Nettleton, D. E.; Grulich, R. E.; Bradner, W. T.; Doyle, T. W.; Arnold, E.; Clardy, J. J. Antibiotics 1981, 34, 1544. Takahashi, K.; Yoshida, M.; Tomita, F.; Shirahata, K. J. Antibiotics 1981, 34, 271. Hirayama, N.; Takahashi, K.; Shirahata, K.; Ohashi, Y.; Sasada, Y. Bull. Chem. Soc. Jpn. 1981, 54, 1338.
6. 2. For structurally related C-aryl glycosides see Findlay, J. A.; Liu, J.-S.; Radics, L.; Can. J. Chem. 1983, 61, 323. Sehgal, S. N.; Czerkawski, H.; Kudelski, A.; Pandev, K.; Saucier, R.; Vezina, C. J. Antibiotics 1983, 36, 355. Balitz, D. M.; O'Herron, F. A.; Bush, J.; Vyas, D. M.; Nettleton, D. E.; Grulich, R. E.; Bradner, W. T.; Doyle, T. W.; Arnold, E.; Clardy, J. J. Antibiotics 1981, 34, 1544. Takahashi, K.; Yoshida, M.; Tomita, F.; Shirahata, K. J. Antibiotics 1981, 34, 271. Hirayama, N.; Takahashi, K.; Shirahata, K.; Ohashi, Y.; Sasada, Y. Bull. Chem. Soc. Jpn. 1981, 54, 1338.
7. 2. For structurally related C-aryl glycosides see Findlay, J. A.; Liu, J.-S.; Radics, L.; Can. J. Chem. 1983, 61, 323. Sehgal, S. N.; Czerkawski, H.; Kudelski, A.; Pandev, K.; Saucier, R.; Vezina, C. J. Antibiotics 1983, 36, 355. Balitz, D. M.; O'Herron, F. A.; Bush, J.; Vyas, D. M.; Nettleton, D. E.; Grulich, R. E.; Bradner, W. T.; Doyle, T. W.; Arnold, E.; Clardy, J. J. Antibiotics 1981, 34, 1544. Takahashi, K.; Yoshida, M.; Tomita, F.; Shirahata, K. J. Antibiotics 1981, 34, 271. Hirayama, N.; Takahashi, K.; Shirahata, K.; Ohashi, Y.; Sasada, Y. Bull. Chem. Soc. Jpn. 1981, 54, 1338.
8. 2. For structurally related C-aryl glycosides see Findlay, J. A.; Liu, J.-S.; Radics, L.; Can. J. Chem. 1983, 61, 323. Sehgal, S. N.; Czerkawski, H.; Kudelski, A.; Pandev, K.; Saucier, R.; Vezina, C. J. Antibiotics 1983, 36, 355. Balitz, D. M.; O'Herron, F. A.; Bush, J.; Vyas, D. M.; Nettleton, D. E.; Grulich, R. E.; Bradner, W. T.; Doyle, T. W.; Arnold, E.; Clardy, J. J. Antibiotics 1981, 34, 1544. Takahashi, K.; Yoshida, M.; Tomita, F.; Shirahata, K. J. Antibiotics 1981, 34, 271. Hirayama, N.; Takahashi, K.; Shirahata, K.; Ohashi, Y.; Sasada, Y. Bull. Chem. Soc. Jpn. 1981, 54, 1338.
9. 2. For structurally related C-aryl glycosides see Findlay, J. A.; Liu, J.-S.; Radics, L.; Can. J. Chem. 1983, 61, 323. Sehgal, S. N.; Czerkawski, H.; Kudelski, A.; Pandev, K.; Saucier, R.; Vezina, C. J. Antibiotics 1983, 36, 355. Balitz, D. M.; O'Herron, F. A.; Bush, J.; Vyas, D. M.; Nettleton, D. E.; Grulich, R. E.; Bradner, W. T.; Doyle, T. W.; Arnold, E.; Clardy, J. J. Antibiotics 1981, 34, 1544. Takahashi, K.; Yoshida, M.; Tomita, F.; Shirahata, K. J. Antibiotics 1981, 34, 271. Hirayama, N.; Takahashi, K.; Shirahata, K.; Ohashi, Y.; Sasada, Y. Bull. Chem. Soc. Jpn. 1981, 54, 1338.
10. 3. For isolation of the aglycone of 1 as a natural product see Misra, R.; Tritch, H. R.; Pandey, R. C. J. Antibiotics 1985, 38, 1280. For syntheses of the aglycone of 1 see Findlay, J. A.; Dalijeet, A.; Murray, P. J.; Rej, R. N. Can. J. Chem. 1987, 65, 427. Macdonald, S. J. F.; McKenzie, T. C.; Hassen, W. D. J. Chem. Soc., Chem. Commun. 1987, 1528. McGee, L. R.; Confalone, P. N. J. Org. Chem. 1988, 53, 3695. Parker, K. A.; Coburn, C. A. J. Org. Chem. 1991, 56, 1666. Also see reference 17.
11. 3. For isolation of the aglycone of 1 as a natural product see Misra, R.; Tritch, H. R.; Pandey, R. C. J. Antibiotics 1985, 38, 1280. For syntheses of the aglycone of 1 see Findlay, J. A.; Dalijeet, A.; Murray, P. J.; Rej, R. N. Can. J. Chem. 1987, 65, 427. Macdonald, S. J. F.; McKenzie, T. C.; Hassen, W. D. J. Chem. Soc., Chem. Commun. 1987, 1528. McGee, L. R.; Confalone, P. N. J. Org. Chem. 1988, 53, 3695. Parker, K. A.; Coburn, C. A. J. Org. Chem. 1991, 56, 1666. Also see reference 17.
12. 3. For isolation of the aglycone of 1 as a natural product see Misra, R.; Tritch, H. R.; Pandey, R. C. J. Antibiotics 1985, 38, 1280. For syntheses of the aglycone of 1 see Findlay, J. A.; Dalijeet, A.; Murray, P. J.; Rej, R. N. Can. J. Chem. 1987, 65, 427. Macdonald, S. J. F.; McKenzie, T. C.; Hassen, W. D. J. Chem. Soc., Chem. Commun. 1987, 1528. McGee, L. R.; Confalone, P. N. J. Org. Chem. 1988, 53, 3695. Parker, K. A.; Coburn, C. A. J. Org. Chem. 1991, 56, 1666. Also see reference 17.
13. 3. For isolation of the aglycone of 1 as a natural product see Misra, R.; Tritch, H. R.; Pandey, R. C. J. Antibiotics 1985, 38, 1280. For syntheses of the aglycone of 1 see Findlay, J. A.; Dalijeet, A.; Murray, P. J.; Rej, R. N. Can. J. Chem. 1987, 65, 427. Macdonald, S. J. F.; McKenzie, T. C.; Hassen, W. D. J. Chem. Soc., Chem. Commun. 1987, 1528. McGee, L. R.; Confalone, P. N. J. Org. Chem. 1988, 53, 3695. Parker, K. A.; Coburn, C. A. J. Org. Chem. 1991, 56, 1666. Also see reference 17.
14. 3. For isolation of the aglycone of 1 as a natural product see Misra, R.; Tritch, H. R.; Pandey, R. C. J. Antibiotics 1985, 38, 1280. For syntheses of the aglycone of 1 see Findlay, J. A.; Dalijeet, A.; Murray, P. J.; Rej, R. N. Can. J. Chem. 1987, 65, 427. Macdonald, S. J. F.; McKenzie, T. C.; Hassen, W. D. J. Chem. Soc., Chem. Commun. 1987, 1528. McGee, L. R.; Confalone, P. N. J. Org. Chem. 1988, 53, 3695. Parker, K. A.; Coburn, C. A. J. Org. Chem. 1991, 56, 1666. Also see reference 17.
15. 4. For syntheses of the aglycone of 2 see McKenzie, T. C.; Hassen, W.; Macdonald, S. J. F. Tetrahedron Lett. 1987, 28, 5435. Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1988, 2517. Deshpande, P. P.; Martin, O. R. Tetrahedron Lett. 1990, 31, 6313. Also see reference 8.
16. 4. For syntheses of the aglycone of 2 see McKenzie, T. C.; Hassen, W.; Macdonald, S. J. F. Tetrahedron Lett. 1987, 28, 5435. Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1988, 2517. Deshpande, P. P.; Martin, O. R. Tetrahedron Lett. 1990, 31, 6313. Also see reference 8.
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