ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img

Controlled chemical synthesis of the enzymically produced eicosanoids 11-, 12-, and 15-HETE from arachidonic acid and conversion into the corresponding hydroperoxides (HPETE)

Cite this: J. Am. Chem. Soc. 1980, 102, 4, 1433–1435
Publication Date (Print):February 1, 1980
https://doi.org/10.1021/ja00524a043
    ACS Legacy Archive

    Article Views

    735

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options

    Note: In lieu of an abstract, this is the article's first page.

    Free first page

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Cited By

    This article is cited by 89 publications.

    1. Vijay Gnanadesikan and E. J. Corey. A Strategy for Position-Selective Epoxidation of Polyprenols. Journal of the American Chemical Society 2008, 130 (25) , 8089-8093. https://doi.org/10.1021/ja801899v
    2. Xiaojun Han,, Sheldon N. Crane, and, E. J. Corey. A Short Catalytic Enantioselective Synthesis of the Vascular Antiinflammatory Eicosanoid (11R,12S)-Oxidoarachidonic Acid. Organic Letters 2000, 2 (22) , 3437-3438. https://doi.org/10.1021/ol006430b
    3. Brian M. Stoltz,, Taichi Kano, and, E. J. Corey. Enantioselective Total Synthesis of Nicandrenones. Journal of the American Chemical Society 2000, 122 (37) , 9044-9045. https://doi.org/10.1021/ja0024892
    4. Xiaojun Han and, E. J. Corey. A Short Catalytic Enantioselective Synthesis of the Proinflammatory Eicosanoid 12(R)-Hydroxy- 5(Z),8(Z),10(E),14(Z)-eicosatetraenoic Acid (12(R)-HETE). Organic Letters 2000, 2 (16) , 2543-2544. https://doi.org/10.1021/ol0062392
    5. Vladimir Kolesnichenko,, Jeffrey J. Luci,, Dale C. Swenson, and, Louis Messerle. W3(μ3-Cl)(μ-Cl)3Cl9n- (n = 2, 3), Discrete Monocapped Tritungsten Clusters Derived from a New Binary Tungsten Chloride, W3Cl10:  Effect of Electron Count on Bonding in Isostructural triangulo M3X13 Clusters1. Journal of the American Chemical Society 1998, 120 (50) , 13260-13261. https://doi.org/10.1021/ja9831958
    6. Rebecca L. Miller,, Kimberly A. Lawler,, Jordan L. Bennett, and, Peter T. Wolczanski. Ditungsten Siloxide Hydrides, [(silox)2WHn]2 (n = 1, 2; silox = tBuSiO), and Related Complexes. Inorganic Chemistry 1996, 35 (11) , 3242-3253. https://doi.org/10.1021/ic9513191
    7. Federica Ianni, Giorgio Saluti, Roberta Galarini, Serena Fiorito, Roccaldo Sardella, Benedetto Natalini. Enantioselective high-performance liquid chromatography analysis of oxygenated polyunsaturated fatty acids. Free Radical Biology and Medicine 2019, 144 , 35-54. https://doi.org/10.1016/j.freeradbiomed.2019.04.038
    8. Anders Vik, Trond Vidar Hansen. Synthetic manipulations of polyunsaturated fatty acids as a convenient strategy for the synthesis of bioactive compounds. Organic & Biomolecular Chemistry 2018, 16 (48) , 9319-9333. https://doi.org/10.1039/C8OB02586J
    9. Tomasz Maciej Stepniewski, Mariona Torrens-Fontanals, Ismael Rodríguez-Espigares, Toni Giorgino, Karoline G. Primdahl, Anders Vik, Yngve Stenstrøm, Jana Selent, Trond Vidar Hansen. Synthesis, molecular modelling studies and biological evaluation of new oxoeicosanoid receptor 1 agonists. Bioorganic & Medicinal Chemistry 2018, 26 (12) , 3580-3587. https://doi.org/10.1016/j.bmc.2018.05.036
    10. Richard C. Larock, Gilson Zeni. Formation of Alkenes by Elimination. 2018, 1-74. https://doi.org/10.1002/9781118662083.cot02-002
    11. Anders Vik, Trond Vidar Hansen. Fatty Acids and their Derivatives. 2016, 130-161. https://doi.org/10.1002/9781118754085.ch3
    12. Tânia Petta, Adriana Secatto, Lúcia Helena Faccioli, Luiz Alberto Beraldo Moraes. Inhibition of inflammatory response in LPS induced macrophages by 9-KOTE and 13-KOTE produced by biotransformation. Enzyme and Microbial Technology 2014, 58-59 , 36-43. https://doi.org/10.1016/j.enzmictec.2014.02.011
    13. E.J. Corey, László Kürti. Examples of Enantioselective Synthesis. 2010, 179-326. https://doi.org/10.1016/B978-0-615-39515-9.50008-4
    14. Albrecht Berkessel, Nadine Vogl. Synthetic Uses of Peroxides. 2009https://doi.org/10.1002/9780470682531.pat0352
    15. Chandra D. Roy, Herbert C. Brown. Monobromoborane - Dimethyl Sulfide—a Highly Promising Reagent for the Regio- and Chemoselective Brominative Cleavage of Terminal Epoxides into Vicinal Bromohydrins. Australian Journal of Chemistry 2007, 60 (2) , 139. https://doi.org/10.1071/CH06408
    16. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush. Hexamethylphosphorous triamide. 2006https://doi.org/10.1002/9780471264194.fos05534
    17. Chandra D. Roy, Herbert C. Brown. Dimethoxyboron bromide – a new, efficient, regio- and chemoselective reagent for the conversion of terminal epoxides into bromohydrins. Journal of Chemical Research 2006, 2006 (10) , 639-641. https://doi.org/10.3184/030823406779173569
    18. Taina Hämäläinen, Afaf Kamal-Eldin. Analysis of Lipid Oxidation Products by NMR Spectroscopy. 2005https://doi.org/10.1201/9781439822395.ch5
    19. Marjorie F Oleksiak, Shu Wu, Carol Parker, Wei Qu, Rachel Cox, Darryl C Zeldin, John J Stegeman. Identification and regulation of a new vertebrate cytochrome P450 subfamily, the CYP2Ps, and functional characterization of CYP2P3, a conserved arachidonic acid epoxygenase/19-hydroxylase. Archives of Biochemistry and Biophysics 2003, 411 (2) , 223-234. https://doi.org/10.1016/S0003-9861(02)00734-8
    20. U.Murali Krishna, M.Muralidhar Reddy, Jianing Xia, J.R. Falck, Michael Balazy. Stereospecific synthesis of trans-arachidonic acids. Bioorganic & Medicinal Chemistry Letters 2001, 11 (18) , 2415-2418. https://doi.org/10.1016/S0960-894X(01)00442-5
    21. Baichun Yang, LeRae Graham, Serguei Dikalov, Ronald P. Mason, John R. Falck, James K. Liao, Darryl C. Zeldin. Overexpression of Cytochrome P450 CYP2J2 Protects against Hypoxia-Reoxygenation Injury in Cultured Bovine Aortic Endothelial Cells. Molecular Pharmacology 2001, 60 (2) , 310-320. https://doi.org/10.1124/mol.60.2.310
    22. Marjorie F. Oleksiak, Shu Wu, Carol Parker, Sibel I. Karchner, John J. Stegeman, Darryl C. Zeldin. Identification, Functional Characterization, and Regulation of a New Cytochrome P450 Subfamily, the CYP2Ns. Journal of Biological Chemistry 2000, 275 (4) , 2312-2321. https://doi.org/10.1074/jbc.275.4.2312
    23. Jianyong Chen, Jorge H. Capdevila, Darryl C. Zeldin, Robert L. Rosenberg. Inhibition of Cardiac L-Type Calcium Channels by Epoxyeicosatrienoic Acids. Molecular Pharmacology 1999, 55 (2) , 288-295. https://doi.org/10.1124/mol.55.2.288
    24. Shu Wu, Weina Chen, Elizabeth Murphy, Scott Gabel, Kenneth B. Tomer, Julie Foley, Charles Steenbergen, John R. Falck, Cindy R. Moomaw, Darryl C. Zeldin. Molecular Cloning, Expression, and Functional Significance of a Cytochrome P450 Highly Expressed in Rat Heart Myocytes. Journal of Biological Chemistry 1997, 272 (19) , 12551-12559. https://doi.org/10.1074/jbc.272.19.12551
    25. Darryl C. Zeldin, Julie Foley, James E. Boyle, Cindy R. Moomaw, Kenneth B. Tomer, Carol Parker, Charles Steenbergen, Shu Wu. Predominant Expression of an Arachidonate Epoxygenase in Islets of Langerhans Cells in Human and Rat Pancreas. Endocrinology 1997, 138 (3) , 1338-1346. https://doi.org/10.1210/endo.138.3.4970
    26. Takuzo Funabiki. Dioxygenases. 1997, 19-104. https://doi.org/10.1007/978-94-011-5442-0_2
    27. Shu Wu, Cindy R. Moomaw, Kenneth B. Tomer, John R. Falck, Darryl C. Zeldin. Molecular Cloning and Expression of CYP2J2, a Human Cytochrome P450 Arachidonic Acid Epoxygenase Highly Expressed in Heart. Journal of Biological Chemistry 1996, 271 (7) , 3460-3468. https://doi.org/10.1074/jbc.271.7.3460
    28. Ihsan Erden. Oxiranes and Oxirenes: Monocyclic. 1996, 97-144. https://doi.org/10.1016/B978-008096518-5.00003-4
    29. . Volume 1 References. 1996, 1215-1369. https://doi.org/10.1016/B978-008096518-5.00247-1
    30. J. Buckingham. E. 1995, 145-191. https://doi.org/10.1007/978-1-4899-3316-4_5
    31. J. Buckingham. H. 1995, 229-276. https://doi.org/10.1007/978-1-4899-3316-4_8
    32. Jean-paul Lellouche, Patrick Quinton. ( E )-(4 R )-Dibenzyloxy Hex-2-enal 1-(Ethylene Acetal): A New Chiral Compound Useful for Eicosanoid Synthesis. Synthetic Communications 1994, 24 (14) , 1979-1988. https://doi.org/10.1080/00397919408010205
    33. Ernst H. Oliw. Oxygenation of polyunsaturated fatty acids by cytochrome P450 monooxygenates. Progress in Lipid Research 1994, 33 (3) , 329-354. https://doi.org/10.1016/0163-7827(94)90029-9
    34. D.C. Zeldin, J. Kobayashi, J.R. Falck, B.S. Winder, B.D. Hammock, J.R. Snapper, J.H. Capdevila. Regio- and enantiofacial selectivity of epoxyeicosatrienoic acid hydration by cytosolic epoxide hydrolase.. Journal of Biological Chemistry 1993, 268 (9) , 6402-6407. https://doi.org/10.1016/S0021-9258(18)53266-X
    35. M. Bartóak. Rearrangements of open‐chain and cyclic ethers. 1993, 843-903. https://doi.org/10.1002/9780470772515.ch15
    36. Jorge H. Capdevila, Shouzou Wei, Anil Kumar, Jun Kobayashi, James R. Snapper, Darryl C. Zeldin, Rama K. Bhatt, John R. Falck. Resolution of dihydroxyeicosanoates and of dihydroxyeicosatrienoates by chiral phase chromatography. Analytical Biochemistry 1992, 207 (2) , 236-240. https://doi.org/10.1016/0003-2697(92)90006-S
    37. Ernst H. Oliw. Enantioselective separation of some polyunsaturated epoxy fatty acids by high-performance liquid chromatography on a cellulose phenylcarbamate (Chiralcel OC) stationary phase. Journal of Chromatography B: Biomedical Sciences and Applications 1992, 583 (2) , 231-235. https://doi.org/10.1016/0378-4347(92)80557-7
    38. J.H. Capdevila, S Wei, J Yan, A Karara, H.R. Jacobson, J.R. Falck, F.P. Guengerich, R.N. DuBois. Cytochrome P-450 arachidonic acid epoxygenase. Regulatory control of the renal epoxygenase by dietary salt loading.. Journal of Biological Chemistry 1992, 267 (30) , 21720-21726. https://doi.org/10.1016/S0021-9258(19)36671-2
    39. Braulio M. Fraga, Fernando García-Tellado, Pedro González, Melchor G. Hernández, James R. Hanson. The chemical and microbiological synthesis of 14-hydroxy-gibberellins. Tetrahedron 1992, 48 (39) , 8491-8504. https://doi.org/10.1016/S0040-4020(01)86597-2
    40. Tadahiro Kato, Toshifumi Hirukawa, Kohji Namiki. Selective terminal olefin oxidation of n-3 polyunsaturated fatty acids. Tetrahedron Letters 1992, 33 (11) , 1475-1478. https://doi.org/10.1016/S0040-4039(00)91651-4
    41. Denis Chemin, Sylvie Gueugnot, Gérard Linstrumelle. An efficient stereocontrolled synthesis of 12(R)-HETE and 12(S)-HETE. Tetrahedron 1992, 48 (21) , 4369-4378. https://doi.org/10.1016/S0040-4020(01)80446-4
    42. Ernst H. Oliw, Howard W. Sprecher. Metabolism of polyunsaturated (n − 3) fatty acids by monkey seminal vesicles: isolation and biosynthesis of omega-3 epoxides. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism 1991, 1086 (3) , 287-294. https://doi.org/10.1016/0005-2760(91)90172-E
    43. K. C. Nicolaou, John Y. Ramphal, Nicos A. Petasis, Charles N. Serhan. Lipoxine und verwandte Eicosanoide: Biosynthese, biologische Eigenschaften und chemische Synthese. Angewandte Chemie 1991, 103 (9) , 1119-1136. https://doi.org/10.1002/ange.19911030907
    44. K. C. Nicolaou, John Y. Ramphal, Nicos A. Petasis, Charles N. Serhan. Lipoxins and Related Eicosanoids: Biosynthesis, Biological Properties, and Chemical Synthesis. Angewandte Chemie International Edition in English 1991, 30 (9) , 1100-1116. https://doi.org/10.1002/anie.199111001
    45. Armando Karara, Elizabeth Dishman, Harry Jacobson, J.R. Falck, Jorge H. Capdevila. Arachidonic acid epoxygenase. FEBS Letters 1990, 268 (1) , 227-230. https://doi.org/10.1016/0014-5793(90)81014-F
    46. J R Falck, S Lumin, I Blair, E Dishman, M V Martin, D J Waxman, F P Guengerich, J H Capdevila. Cytochrome P-450-dependent oxidation of arachidonic acid to 16-, 17-, and 18-hydroxyeicosatetraenoic acids.. Journal of Biological Chemistry 1990, 265 (18) , 10244-10249. https://doi.org/10.1016/S0021-9258(18)86938-1
    47. J.R. Falck, Pendri Yadagiri, Jorge Capdevila. [40] Synthesis of epoxyeicosatrienoic acids and heteroatom analogs. 1990, 357-364. https://doi.org/10.1016/0076-6879(90)87042-2
    48. Terry D. Hammonds, Ian A. Blair, J.R. Falck, Jorge H. Capdevila. Resolution of epoxyeicosatrienoate enantiomers by chiral phase chromatography. Analytical Biochemistry 1989, 182 (2) , 300-303. https://doi.org/10.1016/0003-2697(89)90598-8
    49. A Karara, E Dishman, I Blair, J R Falck, J H Capdevila. Endogenous epoxyeicosatrienoic acids. Journal of Biological Chemistry 1989, 264 (33) , 19822-19827. https://doi.org/10.1016/S0021-9258(19)47185-8
    50. G. D. Snyder, P. Yadagiri, J. R. Falck. Effect of epoxyeicosatrienoic acids on growth hormone release from somatotrophs. American Journal of Physiology-Endocrinology and Metabolism 1989, 256 (2) , E221-E226. https://doi.org/10.1152/ajpendo.1989.256.2.E221
    51. E.J. Corey, Wei-guo Su, Martin B. Cleaver. A simple and efficient synthesis of (7E, 9E, 11Z, 13E)-(5S, 6R, 15S)-trihydroxyeicosatetraenoic acid (6R-lipoxin A). Tetrahedron Letters 1989, 30 (32) , 4181-4184. https://doi.org/10.1016/S0040-4039(01)80684-5
    52. Braulio M. Fraga, James R. Hanson, Melchor G. Hernández, Fernando G. Tellado. The first partial synthesis of 14-hydroxy-gibberellin esters. A titanium (IV)-amide catalysed rearrangement of epoxides. Tetrahedron Letters 1989, 30 (49) , 6899-6902. https://doi.org/10.1016/S0040-4039(01)93383-0
    53. J. Rokach, Y. Guindon, R.N. Young, J. Adams, J.G. Atkinson. Synthesis of the Leukotrienes. 1988, 141-273. https://doi.org/10.1002/9780470129708.ch2
    54. Jorge H. Capdevila, Vijai Kishore, Elizabeth Dishman, Ian A. Blair, J.R. Falck. A novel pool of rat liver inositol and ethanolamine phospholipids contains epoxyeicosatrienoic acids (EETs). Biochemical and Biophysical Research Communications 1987, 146 (2) , 638-644. https://doi.org/10.1016/0006-291X(87)90576-6
    55. J R Falck, V J Schueler, H R Jacobson, A K Siddhanta, B Pramanik, J Capdevila. Arachidonate epoxygenase: identification of epoxyeicosatrienoic acids in rabbit kidney.. Journal of Lipid Research 1987, 28 (7) , 840-846. https://doi.org/10.1016/S0022-2275(20)38651-X
    56. Robert Toto, Arup Siddhanta, Sukumar Manna, Bikash Pramanik, J.R. Faick, Jorge Capdevila. Arachidonic acid epoxygenase: detection of epoxyeicosatrienoic acids in human urine. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism 1987, 919 (2) , 132-139. https://doi.org/10.1016/0005-2760(87)90199-8
    57. K G Proctor, J R Falck, J Capdevila. Intestinal vasodilation by epoxyeicosatrienoic acids: arachidonic acid metabolites produced by a cytochrome P450 monooxygenase.. Circulation Research 1987, 60 (1) , 50-59. https://doi.org/10.1161/01.RES.60.1.50
    58. Paul Mosset, Sukumar Manna, Jacques Viala, J.R. Falck. Isomerization of epoxides to allylic alcohols using methylmagnesium N-cyclohexylisopropylamide. Tetrahedron Letters 1986, 27 (3) , 299-302. https://doi.org/10.1016/S0040-4039(00)84001-0
    59. Marshall E. Spearman, Russell A. Prough, Ronald W. Estabrook, J.R. Falck, Sukumar Manna, Kenneth C. Leibman, Robert C. Murphy, Jorge Capdevila. Novel glutathione conjugates formed from epoxyeicosatrienoic acids (EETs). Archives of Biochemistry and Biophysics 1985, 242 (1) , 225-230. https://doi.org/10.1016/0003-9861(85)90496-5
    60. J.R. Falck, Sukumar Manna, Jacques Viala, Arup K. Siddhanta, Christine A. Moustakis, Jorge Capdevila. Arachidonate epoxygenase: inhibitors and metabolite analogues. Tetrahedron Letters 1985, 26 (19) , 2287-2290. https://doi.org/10.1016/S0040-4039(00)95076-7
    61. E.J. Corey, Wei-guo Su. Simple synthesis and assignment of stereochemistry of lipoxin A. Tetrahedron Letters 1985, 26 (3) , 281-284. https://doi.org/10.1016/S0040-4039(01)80797-8
    62. Georg Fráter, Jean Wenger. Total Synthesis of (±)‐2‐Pupukeanone. Helvetica Chimica Acta 1984, 67 (7) , 1702-1706. https://doi.org/10.1002/hlca.19840670706
    63. Jorge Capdevila, Bikash Pramanik, Joseph L. Napoli, Sukumar Manna, J.R. Falck. Arachidonic acid epoxidation: Epoxyeicosatrienoic acids are endogenous constituents of rat liver. Archives of Biochemistry and Biophysics 1984, 231 (2) , 511-517. https://doi.org/10.1016/0003-9861(84)90415-6
    64. Christoph Rücker, Wolfgang Seppelt, Hans Fritz, Horst Prinzbach. Funktionalisierte Dioxide ( syn ‐1,3) und Trioxide ( syn,syn; syn,anti ) des Tropilidens. Chemische Berichte 1984, 117 (5) , 1801-1833. https://doi.org/10.1002/cber.19841170511
    65. F. D. Gunstone. Reaction of oxygen and unsaturated fatty acids. Journal of the American Oil Chemists' Society 1984, 61 (2) , 441-447. https://doi.org/10.1007/BF02678811
    66. E.J. COREY, DAVID A. CLARK, ANTHONY MARFAT. Structure Elucidation and Total Synthesis of the Leukotrienes. 1984, 13-101. https://doi.org/10.1016/B978-0-12-166750-4.50006-6
    67. Gene W. Holbert, Brian W. Metcalf. Synthesis of α-ethynylhistamine, an inactivator of histidine decarboxylase. Tetrahedron 1984, 40 (7) , 1141-1144. https://doi.org/10.1016/S0040-4020(01)99318-4
    68. J.R. Falck, A.K. Siddhanta, R.W. Estabrook, J. Capdevila, Charles Mioskowski. 5- and 8-HETE production by rat hepatic microsomal cytochrome P-450. Tetrahedron Letters 1984, 25 (14) , 1457-1458. https://doi.org/10.1016/S0040-4039(01)80185-4
    69. J.R. Falck, Sukumar Manna, Jorge Capdevila. Enantiospecific synthesis of methyl 11,12- and 14,15-epoxyeicosatrienoate. Tetrahedron Letters 1984, 25 (23) , 2443-2446. https://doi.org/10.1016/S0040-4039(01)81200-4
    70. E.J. Corey, Chuan Shih, Neng-Yang Shih, Katsuichi Shimoji. Preferential formation of 8-epi-prostaglandin f2α via the corresponding endoperoxide by a biomimetic cyclization. Tetrahedron Letters 1984, 25 (44) , 5013-5016. https://doi.org/10.1016/S0040-4039(01)91105-0
    71. J. Capdevila, Y. Saeki, J. R. Falck. The mechanistic plurality of cytochrome P-450 and its biological ramifications. Xenobiotica 1984, 14 (1-2) , 105-118. https://doi.org/10.3109/00498258409151401
    72. Jack K. Crandall, Marcel Apparu. Base‐Promoted Isomerizations of Epoxides. 1983, 345-443. https://doi.org/10.1002/0471264180.or029.03
    73. J.R. Falck, S. Manna, J. Moltz, N. Chacos, J. Capdevila. Epoxyeicosatrienoic acids stimulate glucagon and insulin release from isolated rat pancreatic islets. Biochemical and Biophysical Research Communications 1983, 114 (2) , 743-749. https://doi.org/10.1016/0006-291X(83)90843-4
    74. P. Kutsky, J.R. Falck, G.B. Weiss, S. Manna, N. Chacos, J. Capdevila. Effects of newly arachidonic acid metabolites on microsomal Ca++ binding, uptake and release. Prostaglandins 1983, 26 (1) , 13-21. https://doi.org/10.1016/0090-6980(83)90070-9
    75. N. Chacos, J. Capdevila, J.R. Falck, S. Manna, C. Martin-Wixtrom, S.S. Gill, B.D. Hammock, R.W. Estabrook. The reaction of arachidonic acid epoxides (epoxyeicosatrienoic acids) with a cytosolic epoxide hydrolase. Archives of Biochemistry and Biophysics 1983, 223 (2) , 639-648. https://doi.org/10.1016/0003-9861(83)90628-8
    76. Kenneth E. Peers, David T. Coxon. Controlled synthesis of monohydroperoxides by α-tocopherol inhibited autoxidation of polyunsaturated lipids. Chemistry and Physics of Lipids 1983, 32 (1) , 49-56. https://doi.org/10.1016/0009-3084(83)90069-5
    77. Walter C. Hubbard, Douglass F. Taber. Analysis of Hydroxy Acids. 1983, 55-63. https://doi.org/10.1007/978-1-4684-4391-2_4
    78. Richard H. Green, Paul F. Lambeth. Leukotrienes. Tetrahedron 1983, 39 (10) , 1687-1721. https://doi.org/10.1016/S0040-4020(01)88677-4
    79. A.S. Rao, S.K. Paknikar, J.G. Kirtane. Recent advances in the preparation and synthetic applications of oxiranes. Tetrahedron 1983, 39 (14) , 2323-2367. https://doi.org/10.1016/S0040-4020(01)91961-1
    80. Sukamar Manna, J.R. Falck, N. Chacos, J. Capdevila. Synthesis of arachidonic acid metabolites produced by purified kidney cortex microsomal cytochrome P-450. Tetrahedron Letters 1983, 24 (1) , 33-36. https://doi.org/10.1016/S0040-4039(00)81319-2
    81. Göran Hansson, Curt Malmsten, Olof Rådmark. Chapter 4 The leukotrienes and other lipoxygenase products. 1983, 127-169. https://doi.org/10.1016/S0167-7306(08)60536-0
    82. Jack Y. Vanderhoek, Robert W. Bryant, J. Martyn Bailey. Regulation of leukocyte and platelet lipoxygenases by hydroxyeicosanoids. Biochemical Pharmacology 1982, 31 (21) , 3463-3467. https://doi.org/10.1016/0006-2952(82)90627-X
    83. E H Oliw, F P Guengerich, J A Oates. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates.. Journal of Biological Chemistry 1982, 257 (7) , 3771-3781. https://doi.org/10.1016/S0021-9258(18)34848-8
    84. J.R. Falck, Sukumar Manna. 8,9-Epoxyarachinodic acid: a cytochrome P-450 metabolite. Tetrahedron Letters 1982, 23 (17) , 1755-1756. https://doi.org/10.1016/S0040-4039(00)86732-5
    85. Paul A Wender, Stephen L Eck. The olefin metathesis/transannular ene sequence: a method for the stereocontrolled synthesis of -decalin derivatives. 3. total synthesis of (±)-warburganal. Tetrahedron Letters 1982, 23 (18) , 1871-1874. https://doi.org/10.1016/S0040-4039(00)87207-X
    86. E.H. Oliw, J.A. Lawson, A.R. Brash, J.A. Oates. Arachidonic acid metabolism in rabbit renal cortex. Formation of two novel dihydroxyeicosatrienoic acids.. Journal of Biological Chemistry 1981, 256 (19) , 9924-9931. https://doi.org/10.1016/S0021-9258(19)68718-1
    87. Naresh Chand, Burton M. Altura. Lipoxygenase pathway and hydroperoxy acids: Possible relevance to aspirin-induced asthma and hyperirritability of airways in asthmatics. Prostaglandins and Medicine 1981, 6 (2) , 249-256. https://doi.org/10.1016/0161-4630(81)90097-5
    88. Ernest W. Colvin. Trimethylsilyl-based reagents. 1981, 288-313. https://doi.org/10.1016/B978-0-408-10831-7.50024-X
    89. E. J. COREY, A. MARFAT, J. R. FALCK, J. O. ALBRIGHT. ChemInform Abstract: CONTROLLED CHEMICAL SYNTHESIS OF THE ENZYMICALLY PRODUCED EICOSANOIDS 11‐, 12‐, AND 15‐HETE FROM ARACHIDONIC ACID AND CONVERSION INTO THE CORRESPONDING HYDROPEROXIDES (HPETE). Chemischer Informationsdienst 1980, 11 (21) https://doi.org/10.1002/chin.198021153

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect