Synthesis of nitrolipids. All four possible diastereomers of nitrooleic acids: (E)- and (Z)-, 9- and 10-nitro-octadec-9-enoic acids

Organic Letters

Volumn 8, Issue 18, 2006, Pages 3931-3934

  Woodcock, Steven R ^a   Marwitz, Adam J V ^a   Bruno, Paulo ^a   Branchaud, Bruce P ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LINOLEIC ACID; NITRO DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

LINOLEIC ACIDS; MOLECULAR STRUCTURE; NITRO COMPOUNDS;

EID: 33748918563     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0613463     Document Type: Article

References (41)

1. Nitric Oxide: Biology and Pathobiology; Ignarro, L. J., Ed.; Academic Press: New York, 2000.
2. (a) Beckman, J. S.; Beckman, T. W.; Chen, J.; Marshall, P. A.; Freeman, B. A. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 1620-1624.
3. (b) Denicola, A.; Freeman, B. A.; Trujillo, M.; Radi, R. Arch. Biochem. Biophys. 1996, 333, 49-58.
4. (a) Gow, A.; Duran, D.; Thom, S. R.; Ischiropoulos, H. Arch. Biochem. Biophys. 1996, 333, 42-48.
5. (b) Schopfer, F. J.; Baker, P. R. S.; Freeman, B. A. Trends Biochem. Sci. 2003, 28, 646-654.
6. (a) Schopfer, F. J.; Baker, P. R. S.; Giles, G.; Chumley, P.; Batthyany, C.; Crawford, J.; Patel, R. P.; Hogg, N.; Branchaud, B. P.; Lancaster, J. R. J.; Freeman, B. A. J. Biol. Chem. 2005, 280, 19289-19297.
7. (b) Baker, P. R. S.; Schopfer, F. J.; Sweeney, S.; Freeman, B. A. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11577-11582.
8. (c) Kalyanaraman, B. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11527-11528.
9. Batthyany, C.; Schopfer, F. J.; Baker, P. R. S.; Duran, R.; Baker, L. M. S.; Huang, Y.; Cervenansky, C.; Branchaud, B. P.; Freeman, B. A. J. Biol. Chem. 2006, 281, 20450-20463.
10. Baker, P. R. S.; Lin, Y.; Schopfer, F. J.; Woodcock, S. R.; Groeger, A. L.; Battyany, C.; Sweeney, S.; Long, M. H.; Iles, K. I.; Baker, L. M. S.; Branchaud, B. P.; Chen, Y. E.; Freeman, B. A. J. Biol. Chem. 2005, 280, 42464-42475.
11. Gorczynski, M. J.; Huang, J.; King, S. B. Org. Lett. 2006, 8 (11), 2305-2308. Lett
12. (a) d'Ischia, M.; Rega, N.; Barone, V. Tetrahedron 1999, 55, 9297-9308.
13. (b) Napolitano, A.; Camera, E.; Picardo, M.; d'Ischia, M. J. Org. Chem. 2000, 65, 4853-4860.
14. (c) Napolitano, A.; Crescenzi, O.; Camera, E.; Giudicianni, I.; Picardo, M.; d'Ischia, M. Tetrahedron 2004, 58, 5061-5067.
15. (d) O'Donnell, V. B.; Eiserich, J. P.; Bloodsworth, A.; Chumley, P. H.; Kirk, M.; Barnes, S.; Darley-Usmar, V. M.; Freeman, B. A. In Methods Enzymol.; Academic Press: New York, 1999; Vol. 301, pp 454-470.
16. Rosini, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.: Pergamon Press: New York, 1991; Vol. 2, pp 321-340.
17. Recent reviews: Luzzio. F. A. Tetrahedron 2001, 57, 915-945.
18. Palomo, C.; Oiarbide, M.; Mielgo, A. Angew. Chem., Int. Ed. 2004, 43, 5442-5444.
19. (a) Acetyl: Soengas, R. G.; Estevez, J. C.; Estevez, R. J. Org. Lett. 2003, 5, 4457-4459.
20. Andersch, J.; Bols, M. Chem.-Eur. J. 2001, 7, 3744-3747.
21. (b) Mesityl: Melton, J.; McMurray, J. E. J. Org. Chem. 1975, 40, 2138-2139.
22. (c) Trifluoroacetyl: Bloom, A. J.; Mellor, J. M. J. Chem. Soc., Perkin Trans. 1 1987, 2737-3741.
23. (d) DCC: Knochel, P.; Seebach, D. Synthesis 1982, 1017-1018.
24. (a) Tranchepain, I.; Le Berre, F.; Dureault, A.; Le Merrer, Y.; Depezay, J. C. Tetrahedron 1989, 45, 2057-2065.
25. (b) Buchanan, G. W.; Smits, R.; Munteanu, E. J. Fluorine Chem. 2003, 123 (2), 255-259.
26. Kornblum, N.; Ungnade, H. E. Org. Synth. Coll. Vol. IV, 724-727.
27. Ono, N.; Maruyama, K. Bull. Chem. Soc. Jpn. 1988, 61, 4470-4472.
28. (a) Kamimura, A.; Ono, N. Tetrahedron Lett. 1989, 30, 731-734.
29. (b) Kamimura, A.; Sasatani, H.; Hashimoto, T.; Kawai, T.; Hori, K.; Ono, N. J. Org. Chem. 1990, 55, 2437-2442.
30. Myers, A. G.; Barbay, J. K.; Zhong, B. J. Am. Chem. Soc. 2001, 123, 7207-7219.
31. (a) Honda, M.; Morita, H.; Nagakura, I. J. Org. Chem. 1997, 62, 8932-8936.
32. (b) Friedrich-Bochnitschek, S.; Waldmann, H.; Kunz, H. J. Org. Chem. 1989, 54, 751-756.
33. (c) Jeffrey, P. D.; McCombie, S. W. J. Org. Chem. 1982, 47, 587-590.
34. (a) Hey, H.; Arpe, H.-J. Angew. Chem., Int. Ed. Engl. 1973, 12, 928-929.
35. (b) Fletcher, S. P.; Dumur, F.; Pollard, M. M.; Feringa, B. L. Science 2005, 310, 80-82.
36. Kharisov, R. Ya.; Botsman, O. V.; Botsman, L. P.; Ishmuratova, N. M.; Ishmuratov, G. Yu.; Tolstikov, G. A. Chem. Nat. Compd. 2002, 38 (2), 145-148.
37. Stanetty, P.; Kremslehner, M. Tetrahedron Lett. 1998, 39, 811-812.
38. (a) Ono, N.; Kamimura, A.; Kawai, T.; Kaji, A. J. Chem. Soc., Chem. Commun. 1987, 1550-1551.
39. (b) Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1973, 95, 2697-2699. See also ref 14.
40. Note that in contrast to their IUPAC nomenclature the (Z)-isomers are sometimes referred to as "trans" nitrated fatty acids to identify the parent fatty acid structural motif: see ref 6.
41. It is also possible to form the β-nitroselenide, deprotect, then oxidize and eliminate the phenylselenous acid.