Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin

Journal of the American Chemical Society

Volumn 126, Issue 27, 2004, Pages 8396-8398

  Tichenor, Mark S ^a   Kastrinsky, David B ^a   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DNA; DUOCARMYCIN A; DUOCARMYCIN SA; NATURAL PRODUCT; UNCLASSIFIED DRUG; YATAKEMYCIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DNA ALKYLATION; DNA BINDING; DRUG ISOLATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STREPTOMYCES; SYNTHESIS;

INDOLES; PYRROLES; STEREOISOMERISM; STREPTOMYCES;

EID: 3142723437     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0472735     Document Type: Article

References (24)

1. Igarashi, Y.; Futamata, K.; Fujita, T.; Sekine, A.; Senda, H.; Naoki, H.; Furumai, T. J. Antibiot. 2003, 56, 107-113.
2. Martin, D. G.; Biles, C.; Gerpheide, S. A.; Hanka, L. J.; Krueger, W. C.; McGovren, J. P.; Mizsak, S. A.; Neil, G. L.; Stewart, J. C.; Visser, J. J. Antibiot. 1981, 34, 1119-1125.
3. Takahashi, I.; Takahashi, K.; Ichimura, M.; Morimoto, M.; Asano, K.; Kawamoto, I.; Tomita, F.; Nakano, H. J. Antibiot. 1988, 41, 1915-1917.
4. Ichimura, M.; Ogawa, T.; Takahashi, K.; Kobayashi, E.; Kawamoto, I.; Yasuzawa, T.; Takahashi, I.; Nakano, H. J. Antibiot. 1990, 43. 1037-1038.
5. Yatakemycin: Parrish, J. P.; Kastrinsky, D. B.; Wolkenberg, S. E.; Igarashi, Y.; Boger, D. L. J. Am. Chem. Soc. 2003, 125, 10971-10976.
6. CC-1065: Hurley, L. H.; Lee, C.-S.; McGovren, J. P.; Warpehoski, M. A.; Mitchell, M. A.; Kelly, R. C.; Aristoff, P. A. Biochemistry 1988, 27, 3886-3892.
7. Duocarmycin A: Boger, D. L.; Ishizaki, T.; Zarrinmayeh, H.; Munk, S. A.; Kitos, P. A.; Suntornwat, O. J. Am. Chem. Soc. 1990, 112, 8961-8971.
8. Duocarmycin SA: Boger, D. L.; Johnson, D. S.; Yun, W. J. Am. Chem. Soc. 1994, 116, 1635-1656.
9. Review: Boger, D. L.; Johnson, D. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1438-1474.
10. Boger, D. L.; Bollinger, B.; Hertzog, D. L.; Johnson, D. S.; Cai, H.; Mesini, P.; Garbaccio, R. M.; Jin, Q.; Kitos, P. A. J. Am. Chem. Soc. 1997, 119, 4987-4998.
11. Review: Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. A. Chem Rev. 1997, 97, 787-828.
12. Boger, D. L.; Machiya, K.; Hertzog, D. L.; Kitos, P. A.; Holmes, D. J. Am. Chem. Soc. 1993, 115, 9025-9036.
13. Tietze, L. F.; Haunert, F.; Feuerstein, T.; Herzig, T. Eur. J. Org. Chem. 2003, 3, 562-566.
14. 2, 10% Pd/C, MeOH, 1 h, 99%) of 6-benzyloxy-5- methoxyindole-2-carboxylic acid (Spectrum Chemical).
15. Kato, S.; Morie, T. J. Heterocycl. Chem. 1996, 33, 1171-1178.
16. (a) Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958, 1, 23-65.
17. (b) Kraus, G. A.; Yue, S.; Sy, J. J. Org. Chem. 1985, 50, 283-284.
18. Barbero, M.; Cadamuro, S.; Degani, I.; Fochi, R.; Gatti, A.; Regondi, V. Synthesis 1988, 300-302.
19. Jordan, F.; Kudzin, Z.; Witczak, Z.; Hoops, P. J. Org. Chem. 1986, 51, 571-573.
20. (a) Bolton, R. E.; Moody, C. J.; Rees, C. W.; Tojo, G. J. Chem. Soc., Perkin Trans. 1 1987, 931-935.
21. (b) Boger, D. L.; Coleman, R. S. J. Am. Chem. Soc. 1987, 109, 2717-2727.
22. (c) Boger, D. L.; Coleman, R. S.; Invergo, B. J.; Sakya, S. M.; Ishizaki, T.; Munk, S. M.; Zarrinmayeh, H.; Kitos, P. A.; Thompson. S. C. J. Am. Chem. Soc. 1990, 112, 4623-4632.
23. 2, 10% Pd/C, 25 °C, 1 h, 83%) provided 35. See: MacKenzie, A. R.; Moody, C. J.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1983, 22, 1372-1373.
24. 50 = 5 pM (indistinguishable) for both (+)- and ent-(-)-1.