Short-step and scalable synthesis of (±)-cytoxazone

Bioscience, Biotechnology and Biochemistry

Volumn 69, Issue 1, 2005, Pages 145-148

  Asano, Masayoshi ^a   Nagasawa, Chiaki ^a   Suzuki, Masumi ^a   Nishiyama, Shigeru ^a   Sugai, Takeshi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Azidohydroxylation; Cytoxazone; Deaminocyclization; Nitrosation; Oxazolidinone

Indexed keywords

ALCOHOLS; BIOCHEMISTRY; OLEFINS; OXIDATION; SODIUM COMPOUNDS;

AZIDOHYDROXYLATION; CYTOKINE MODULATOR; EPOXIDATION; RACEMIC CYTOXAZONE;

BIOSYNTHESIS;

CYTOXAZONE; OXAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; STEREOISOMERISM; SYNTHESIS;

MOLECULAR STRUCTURE; OXAZOLES; STEREOISOMERISM;

EID: 15244354409     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.69.145     Document Type: Article

References (20)

1. Kakeya, H., Morishita, M., Kobinata, K., Osono, M., Ishizuka, M., and Osada, H., Isolation and biological activity of a novel cytokine modulator, cytoxazone. J. Antibioics, 51, 1126-1128 (1998).
2. Kakeya, H., Morishita, M., Koshino, H., Morita, T., Kobayashi, K., and Osada, H., Cytoxazone: A novel cytokine modulator containing a 2-oxazolidinone ring produced by Streptomyces sp. J. Org. Chem., 64, 1052-1053 (1999).
3. Sakamoto, Y., Shiraishi, A., Seonhee, J., and Nakata, T., Stereoselective syntheses of cytoxazone, a novel cytokine modulator, and its stereoisomers. Tetrahedron Lett., 40, 4203-4206 (1999).
4. Seki, M., and Mori, K., Synthesis of (-)-cytoxazone, a novel modulator isolated from Streptomyces sp. Eur. J. Org. Chem., 2965-2967 (1999).
5. Park, J. N., Ko, S. Y., and Koh, H. Y., Synthetic application of the cyclic iminocarbonate rearrangement: enantioselective syntheses of chloamphenicol and 4-epicytoxazone. Tetrahedron Lett., 41, 5553-5556 (2000).
6. Madhan, A., Kumar, A. R., and Rao, B. V., Stereoselective synthesis of (-)-cytoxazone. Tetrahedron: Asymmetry, 12, 2009-2011 (2001).
7. Hamersak, Z., Ljubovic, E., Mercep, M., Mesic, M., and Sunjic, V., Chemoenzymatic synthesis of all four cytoxazone stereoisomers. Synthesis, 1989-1992 (2001).
8. Carda, M., González, F., Sánchez, R., and Marco, J. A., Stereoselective synthesis of (-)-cytoxazone. Tetrahedron: Asymmetry, 13, 1005-1010 (2002).
9. N2 cyclization of N-Boc-β-amino alcohols. Tetrahedron Lett., 44, 6323-6325 (2003).
10. Carter, P. H., LaPorte, J. R., Scherle, P. A., and Decicco, C. P., A new synthesis of cytoxazone and its diastereomers provides key initial SAR information. Bioorg. Med. Chem. Lett., 13, 1237-1239 (2003).
11. Miyata, O., Koizumi, T., Asai, H., Iba, R., and Naito, T., Imino 1,2-Wittig rearrangement of hydroximates and its application to synthesis of cytoxazone. Tetrahedron, 60, 3893-3914 (2004).
12. Milicevic, S., Matovic, R., and Saicic, R. N., Stereoselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone. Tetrahedron Lett., 45, 955-957 (2004).
13. Davies, S. G., Hughes, D. G., Nicholson, R. L., Smith, A. D., and Wright, A. J., Asymmetric synthesis of (4R,5R)-cytoxazone and (4R,5S)-epi-cytoxazone. Org. Biomol. Chem., 2, 1549-1553 (2004).
14. Payne, G. B., Deming, P. H., and Williams, P. H., Reactions of hydrogen peroxide. VII. Alkali-catalyzed epoxidation and oxidation using a nitrile as co-reactant. J. Org. Chem., 26, 659-663 (1961).
15. Chini, M., Crotti, P., and Macchia, F., Efficient metal salt catalyzed azidolysis of epoxides with sodium azide in acetonitrile. Tetrahedron Lett., 31, 5641-5644 (1990).
16. Knouzi, N., Vaultier, M., and Carrie, R., Reduction d'azides par la triphenylphosphine en presence d'eau: une methode generale et chimioselective d'acces aux amines primaires. Bull. Soc. Chim. Fr., 815-819 (1985).
17. Knölker, H.-J., and Braxmeier, T., Isocyanates Part 5. Synthesis of chiral oxazolidin-2-ones and imidazolidin-2-ones via DMAP-catalyzed isocyanation of amines with di-tert-butyl dicarbonate. Tetrahedron Lett., 39, 9407-9410 (1998).
18. Miyahara, M., Nakadate, M., and Kamiya, S., Cyclization of (2-hydroxyethyl)urea derivatives to give 3-nitroso-2-oxazolidinones under usual nitrosation conditions. Chem. Pharm. Bull., 33, 497-502 (1985).
19. Suzuki, M., Yamazaki, T., Ohta, H., Shima, K., Ohi, K., Nishiyama, S., and Sugai, T., N-Carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction. Synlett, 189-192 (2000).
20. Legters, J., Thijs, L., and Zwanenburg, B., A convenient synthesis of optically Active 1H-aziridine-2-carboxylic acids (esters). Tetrahedron Lett., 30, 4881-4884 (1989).