A concise synthesis of (-)-cytoxazone and its stereoisomers via imino 1,2-Wittig rearrangement

Synlett

Volumn , Issue 12, 1999, Pages 1915-1916

  Miyata, Okiko ^a   Hiroshi, Asai ^a   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

2 hydroxy oxime ether; Cytokine modulator; Hydroximate; Oxazolidinone; Wittig rearrangement

Indexed keywords

CYTOKINE; CYTOXAZONE; OXAZOLIDINONE DERIVATIVE; OXIME DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYTOKINE PRODUCTION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; REACTION ANALYSIS;

EID: 0344578018     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2992     Document Type: Article

References (12)

1. Kakeya, H.; Morishita, M.; Kobinata, K.; Osono, M.; Osada, H. J. Antibiot. 1998, 51, 1126.
2. Kakeya, H.; Morishita, M.; Koshino, H.; Morita, T.; Kobayashi, K.; Osada, H. J. Org. Chem. 1999, 64, 1052.
3. Sakamoto, Y.; Shiraishi, A.; Seonhee, J.; Nakata, T. Tetrahedron Lett. 1999,40, 4203.
4. Miyata, O.; Koizumi, T.; Ninomiya, I.; Naito, T. J. Org. Chem. 1996, 61, 9078.
5. (a) Shimizu, M.; Tsukamoto, K.; Fujisawa, T. Tetrahedron Lett. 1997, 38, 5193.
6. (b) Boukhris, S.; Souizi, A. Tetrahedron Lett. 1999, 40, 1669.
7. (c) Barluenga, J.; Aguilar, E.; Fustero, S.; Olano, B.; Viado, A. L. J. Org. Chem. 1992, 57, 1291.
8. (d) Narasaka, K.; Ukaji, Y.; Yamazaki, S. Bull. Chem. Soc. Jpn. 1986, 59, 525.
9. Knölker, H. J.; Braxmeier, T. Tetrahedron Lett. 1998, 39, 9407.
10. 3, 500 MHz) δ:2.44 (1H. br s), 3.71 (1H, br d, J = 13Hz), 3.82 (3H, s), 3.96 (1H. br d, J = 13 Hz), 4.39 (1H, dt, J = 7.5, 3.5 Hz), 4.83 (1H, d, J = 7.5 Hz,), 5.49 (1H, br s), 6.92 (2H, m), 7.28 (2H, m).
11. 23-75.7 (c 1.0, MeOH)).
12. 29+75.0 (c 0.52, MeOH).