Isoprekinamycin is a diazobenzo[a]fluorene rather than a diazobenzo[b]fluorene [14]

Journal of the American Chemical Society

Volumn 122, Issue 34, 2000, Pages 8325-8326

  Proteau, Philip J ^a   Li, Yongfu ^a   Chen, Jiong ^a   Williamson, R Thomas ^a   Gould, Steven J ^a,c   Laufer, Radoslaw S ^b   Dmitrienko, Gary I ^b  

^a OREGON STATE UNIVERSITY   (United States)

^b UNIVERSITY OF WATERLOO   (Canada)

^c MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; ISOPREKINAMYCIN; KINAMYCIN DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; LETTER; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STREPTOMYCES; STRUCTURE ANALYSIS;

EID: 0034734361     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001631w     Document Type: Letter

References (17)

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3. Gould, S. J. Chem. Rev. 1997, 97, 2499-2509.
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8. (c) DeFrutos, O; Echevarren, A. M. Tetrahedron Lett. 1997, 38, 7941-7942.
9. 8 leads to the conclusion that CpdB possesses the prekinamycin structure 3, and the work described herein leads to the conclusion that CpdA must possess the isoprekinamycin structure 4.
10. Gould, S. J.; Chen, J.; Cone, M. C.; Gore, M. P.; Melville, C. R.; Tamayo, N. J. Org. Chem. 1996, 61, 5720-5721.
11. Akiyama, T.; Nakamura, K. T.; Takahashi, Y.; Naganawa, H.; Muraoka, Y.; Aoyagi, T. J. Antibiot. 1998, 51, 586-588.
12. For full details see the Supporting Information.
13. Seaton, P. J.; Gould, S. J. J. Antibiot. 1989, 42, 189-197.
14. Laufer, R. S.; Dmitrienko, G. I. Manuscript submitted to Org. Lett.
15. 2]acetate is consistent with the benzo[a]fluorene ring system arising from a benzo[b]-fluorene intermediate.
16. 2]acetate was performed as described previously for the kinamycins. Sato, Y.; Gould. S. J. J. Am. Chem. Soc. 1986, 108, 4625-4631.
17. Moore, H. W.; Wikholm, R. J. In The Chemistry of the Quinonoid Compounds, Part 1; Patai, S., Ed.; John Wiley and Sons: London 1974; pp 441-446.