An efficient synthesis of antibiotic SF-2312 (3-dihydroxyphosphoryl-1,5- dihydroxy-2-pyrrolidone)

Heterocycles

Volumn 82, Issue 2, 2010, Pages 1675-1683

  Hanaya, Tadashi ^a   Itoh, Chika ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952763083     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-10-S(E)80     Document Type: Article

References (15)

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2. Y. Kuroda, M. Okuhara, T. Goto, M. Okamaoto, H. Terano, M. Kohsaka, H. Aoki, and H. Imanaka, J. Antibiot., 1980, 33, 29.
3. M. Okuhara, Y. Kuroda, T. Goto, M. Okamoto, H. Terano, M. Kohsaka, H. Aoki, and H. Imanaka, J. Antibiot., 1980, 33, 13.
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5. H. Jomaa, J. Wiesner, S. Sanderbrand, B. Altincicek, C. Weidemeyer, M. Hintz, I. Turbachova, M. Eberl, J. Zeidler, H. K. Lichtenthaler, D. Soldati, and E. Beck, Science, 1999, 285, 1573
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7. M. Courtois, Z. Mincheva, F. Andreu, M. Rideau, and M. C. Viaud-Massuard, J. Enzyme Inhib. Med. Chem., 2004, 19, 559
8. L. Kuntz, D. Tritsch, C. Grrosdemange-Billiard, A. Hemmerlin, A. Willem, T. J. Bach, and M. Rohmer, Biochem. J., 2005, 386, 127
9. T. Haemers, J. Wiesner, R. Busson, H. Jomaa, and S. Van Calenbergh, Eur. J. Org. Chem, 2006, 3856.
10. As analogs of SF-2312 (3), 1-hydroxy-3-phosphorylpyrrolidin-2,5-dione derivatives have been prepared: W. Owotoki, D. Geffken, and T. Kurz, Aust. J. Chem., 2006, 59, 283.
11. K. Ohba, H. Watabe, J. Yoshida, T. Shomura, M. Sezaki, and T. Ishikawa, Jpn. Patent, 60,224,493, 1985
12. (Chem. Abstr, 1986, 104, 107918y).
13. Most of physico-chemical properties of 3 are reported as the corresponding mono sodium salt: K. Ohba, Y. Sato, T. Sasaki, and M. Sezaki, Sci. Reports of Meiji Seika Kaisha, 1986, 25, 18.
14. T. Janecki, E. Błaszczyk, K. Studzian, M. Różalski, U. Krajewska, and A. Janecka, J. Med. Chem., 2002, 45, 1142.
15. Although 1H NMR spectrum of an isomeric mixture (ca. 2:3) of the natural 3 is shown in Ref. 6, the cis-and trans-structures of the isomers are not assigned. The isomeric structures of the synthetic 3 and 9-11 were assigned by comparison to the 1H NMR data for the isomers of 7 and 8 having the similar characteristic tendency of the corresponding coupling constants and chemical shifts (Table 1). The precise conformations of these compounds are currently under consideration.