Studies toward Thiostrepton Antibiotics: Assembly of the Central Pyridine-Thiazole Cluster of Micrococcins

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3804-3805

  Ciufolini, Marco A ^a   Shen, Yong Chun ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MICROCOCCIN P 1; THIAZOLE DERIVATIVE; THIOSTREPTON; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030850837     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9704422     Document Type: Article

References (19)

1. Structure: (a) Bycroft, B. W.; Gowland, M. S. J. Chem. Soc., Chem. Commun. 1978, 256.
2. Review: (b) Pestka, S. In Antibiotics; Corcoran, J. W., Hahn, F. E., Eds.; Springer-Verlag: New York, 1975; Vol. 3, p 480 ff.
3. Review: Pestka, S.; Bodley, J. W. In Antibiotics; Corcoran, J. W., Hahn, F. E., Eds.; Springer-Verlag: New York, 1975; Vol. 3, p 531 ff.
4. (a) Rosendahl, G.; Douthwaite, S. Nucleic Acids Res. 1994, 22, 357.
5. (b) Cundliffe, E.; Thompson, J. Eur. J. Biochem. 1981, 118, 47.
6. (a) Murakami, T.; Holt, T. G.; Thompson, C. T. J. Bacteriol. 1989, 171, 1459.
7. (b) Holmes, D, G.; Caso, J. L.; Thompson, C. T. EMBO J. 1993, 8, 3183.
8. Yun, B.-S.; Hidaka, T.; Furihata, K.; Seto, H. J. Antibiot. 1994, 47, 510.
9. Kelly, T. R.; Jagoe, C.T.; Gu, Z. Tetrahedron Lett. 1991, 52, 4263.
10. Cf. (a) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082. (b) Ciufolini, M. A.; Shen, Y. C.; Bishop, M. J. J. Am. Chem. Soc. 1995, 117, 12460. (c) Ciufolini, M. A. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, p 1.
11. Cf. (a) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082. (b) Ciufolini, M. A.; Shen, Y. C.; Bishop, M. J. J. Am. Chem. Soc. 1995, 117, 12460. (c) Ciufolini, M. A. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, p 1.
12. Cf. (a) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082. (b) Ciufolini, M. A.; Shen, Y. C.; Bishop, M. J. J. Am. Chem. Soc. 1995, 117, 12460. (c) Ciufolini, M. A. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, p 1.
13. Thomsen, I.; Clausen, K.; Scheibye, S.; Lawesson, S. O. In Organic Syntheses; Freeman, J. P., Ed.; John Wiley & Sons: New York, NY, 1990; Collect. Vol. VII, p 372 and references cited therein.
14. Prepared according to: Attenburrow, J.; Cameron, A. F. B.; Chapman, J. H.; Evans, R. M.; Hems, B. A.; Jansen, A. B. A.; Walker, T. J. Chem. Soc. 1952, 1094. Other oxidants (PCC, PDC, Swern, TPAP/ NMO) gave poor results.
15. 4.
16. 4.
17. A complex mixture of products was obtained when this reaction was run under standard conditions (refluxing xylenes, ca. 135°C).
18. This material existed as a 1:3 ratio mixture of ketone and one geometric isomer of the enol form (NMR, probably the Z isomer due to intramolecular H bonding).
19. Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1987, 28, 4185.