Intramolecular sulfur-assisted NaBH4 reduction of esters synthesis of 5-oxo-ETE and 5-oxo-12-HETE

Tetrahedron Letters

Volumn 41, Issue 30, 2000, Pages 5653-5657

  Khanapure, Subhash P ^a   Saha, Goutam ^a   Sivendran, Sashikala ^a   Powell, William S ^b   Rokach, Joshua ^a  

^a FLORIDA INSTITUTE OF TECHNOLOGY   (United States)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

5 oxo ETE; MeOH; NaBH4

Indexed keywords

ARTICLE; INFLAMMATION; REDUCTION; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0034702579     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00943-6     Document Type: Article

References (17)

1. Stamatiou, P.; Hamid, Q.; Taha, R.; Yu, W.; Issekutz, T. B.; Rokach, J.; Khanapure, S. P.; Powell, W. S. J. Clin. Invest. 1998, 102, 2165-2172.
2. Powell, W. S.; Gravel, S.; Khanapure, S. P.; Rokach, J. Blood 1999, 93, 1086-1096.
3. Khanapure, S. P.; Shi, X. X.; Powell, W. S.; Rokach, J. J. Org. Chem. 1998, 63, 337-342.
4. Khanapure, S. P.; Shi, X. X.; Powell, W. S.; Rokach, J. J. Org. Chem. 1998, 63, 4098-4102.
5. Khanapure, S. P.; Powell, W. S.; Rokach, J. J. Org. Chem. 1998, 63, 8976-8982.
6. Unpublished results 1975.
7. Barnett, J. E. G.; Kent, P. W. J. Chem. Soc. 1963, 2743-2747.
8. Tsuboi, S.; Furutani, H.; Utaka, M.; Takeda, A. Tetrahedron Lett. 1987, 28, 2709-2712.
9. 3) δ 173.93, 72.46, 69.44, 51.68, 39.83, 39.23, 37.66, 33.92, 21.93.
10. Soai, K.; Oyamada, H.; Takase, M.; Ookawa, A. Bull. Chem. Soc. Jpn. 1984, 57, 1948-1953.
11. Soai, K.; Oyamada, H.; Ookawa, A. Synthetic Commun. 1982, 12, 463-467.
12. Thomas, E. J.; Williams, A. C. J. Chem. Soc., Chem. Commun. 1987, 992-994.
13. Sasaki, N. A.; Hashimoto, C.; Potier, P. Tetrahedron Lett. 1987, 28, 6069-6072.
14. Brown, M. S.; Rapoport, H. J. Org. Chem. 1963, 28, 3261-3263.
15. Santaniello, E.; Ferraboschi, P.; Sozzani, P. J. Org. Chem. 1981, 46, 4584-4585.
16. Zanka, A.; Ohmori, H.; Okamoto, T. Synlett 1999, 1636-1638.
17. Bell, R. A.; Gravestock, M. B. Can. J. Chem. 1969, 47, 2099-2102.