Asymmetric total synthesis of (+)-K01-0509 B: Determination of absolute configuration

Organic Letters

Volumn 8, Issue 24, 2006, Pages 5577-5580

  Tsuchiya, Satoshi ^a   Sunazuka, Toshiaki ^a,b   Hirose, Tomoyasu ^b   Mori, Ryuma ^a   Tanaka, Toshiaki ^a   Iwatsuki, Masato ^b   Omura, Satoshi ^a,b  

^a KITASATO UNIVERSITY   (Japan)

^b KITASATO INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; COBALT; EPOXIDE; ETHANOLAMINE DERIVATIVE; GUANIDINE DERIVATIVE; K01 0509 B; K01-0509 B; RP333; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; CYCLIZATION; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; STREPTOMYCES; SYNTHESIS;

ANTI-BACTERIAL AGENTS; CATALYSIS; COBALT; CYCLIZATION; EPOXY COMPOUNDS; ETHANOLAMINES; GUANIDINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; STEREOISOMERISM; STREPTOMYCES;

EID: 33846111293     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062282z     Document Type: Article

References (26)

1. Iwatsuki, M.; Tomoda, H.; Uchida, R.; Yoshijima, H.; Kim, Y.-P.; Ui, H.; Matsumoto, A.; Takahashi, Y.; Abe, A.; Omura, S. J. Antibiot. 2006, submitted.
2. Cornelis, G. R.; Gijsegem, F. V. Annu. Rev. Microbiol. 2000, 54, 735-774.
3. (a) Hueck, C. J. Microbiol. Mol. Biol. Rev. 1998, 62, 379-433.
4. (b) Cheng, L. W.; Schneewind, O. Trends Microbiol. 2000, 8, 214-220.
5. (c) Abe, A.; Heczko, U.; Hegele, R. G.; Finlay, B. B. J. Exp. Med. 1998, 188, 1907-1916.
6. (d) DeVinney, R.; Gauthier, A.; Abe, A.; Finlay, B. B. Cell Mol. Life Sci. 1999, 55, 961-976.
7. Ōmura, S.; Tomoda, H.; Abe, A.; Iwatsuki, M.; Takahashi, Y. PCT WO 2006/304843 A1, March 7, 2006.
8. Omura, S.; Tomoda, H.; Abe, A.; Iwatsuki, M.; Takahashi, Y. PCT WO 2005/090384 A1, September 29, 2005.
9. (a) Horii, S.; Kameda, Y. J. Antibiot. 1968, 21, 665-667.
10. (b) Higashide, E.; Hatano, K.; Shibata, M.; Nakazawa, K. J. Antibiot. 1968, 21, 126-137.
11. (c) Higashide, E.; Hatano, K.; Shibata, M.; Nakazawa, K. J. Antibiot. 1968, 21, 138-146.
12. (a) Hamada, M.; Kondo, J.; Yokoyama, T.; Miura, K.; Iinuma, K.; Yamamoto, H.; Maeda, K.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1974, 27, 81-83.
13. (b) Iinuma, K.; Kondo, S.; Maeda, K.; Umezawa, H. J. Antibiot. 1975, 28, 613-615.
14. Garcia, A.; Vázquez, M. J.; Quiñoá, E.; Riguera, R.; Debitus, C. J. Nat. Prod. 1996, 59, 782-785.
15. Nacro, K.; Baltas, M.: Gorrichon, L. Tetrahedron 1999, 55, 14013-14030.
16. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C. K. J. Am. Chem. Soc. 1989, 111, 5335-5340.
17. Finan, J. M.; Kishi, Y. Tetrahedron Lett. 1982, 27, 2719-2722.
18. (a) Trost, B. M.; Yeh, V. S. C. Angew. Chem., Int. Ed. 2002, 41, 861-863.
19. (b) Trost, B. M.; Yeh, V. S. C.; Ito, H.; Bremeyer, N. Org. Lett. 2002, 4, 2621-2623.
20. (a) Kogami, Y.; Nakajima, T.; Ashizawa, T.; Kezuka, S.; Ikeno, T.; Yamada, T. Chem. Lett. 2004, 33, 614-615.
21. (b) Kogami, Y.; Nakajima, T.; Ikeno, T.; Yamada, T. Synthesis 2004, 12, 1947-1950.
22. The synthesis of Mosher's ester of 6 and the results of the analysis are described in the Supporting Information.
23. (a) Bernatowicz, M. B.; Wu, Y.; Matsueda, G. R. Tetrahedron Lett. 1993, 34, 3389-3392.
24. (b) Drake, B.; Patek, M.; Lebl, M. Synthesis 1994, 2, 579-582.
25. Kronenthal, D. R.; Han, C. Y.; Taylor, M. K. J. Org. Chem. 1982, 47, 2765-2768.
26. 1H NMR spectra and HPLC charts of synthetic compounds and natural K01-0509 B are given in the Supporting Information.