PHENYLSELENYLATION OF ARACHIDONIC-ACID AS A ROUTE TO INTERMEDIATES FOR LEUKOTRIENE SYNTHESIS - ISOMERIZATION OF CONJUGATED DIENES DURING SELENOXIDE ELIMINATION

被引:12
作者
BALDWIN, JE
REED, NV
THOMAS, EJ
机构
关键词
D O I
10.1016/0040-4020(81)85063-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methyl (5SR, 6SR)-5-hydroxy-6-phenylselenyleicosa-cis,cis,cis-8,11,14-trienoate, available in 2 steps from arachidonic acid, undergoes oxidative deselenylation to give selectively either methyl (5SR)-5-hydroxyeicosa-trans,trans,cis,cis-6,8,11,14-tetraenoate or its cis-8 isomer, depending upon the reaction conditions. [Leukotrienes are implicated in the biosynthesis of slow-reacting substances, important agonists in hypersensitivity.].
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页码:263 / 267
页数:5
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共 28 条
[1]  
AUSTEN K F, 1978, Journal of Immunology, V121, P793
[2]   ARACHIDONIC-ACID METABOLISM IN POLYMORPHONUCLEAR LEUKOCYTES .5. UNSTABLE INTERMEDIATE IN FORMATION OF DIHYDROXY ACIDS [J].
BORGEAT, P ;
SAMUELSSON, B .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1979, 76 (07) :3213-3217
[3]   ARACHIDONIC-ACID METABOLISM IN POLYMORPHONUCLEAR LEUKOCYTES .3. EFFECTS OF IONOPHORE-A23187 [J].
BORGEAT, P ;
SAMUELSSON, B .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1979, 76 (05) :2148-2152
[4]  
BORGEAT P, 1979, J BIOL CHEM, V254, P2643
[5]   NEW ROUTE TO BICYCLIC LACTONES - USE OF BENZENESELENENYL CHLORIDE [J].
CLIVE, DLJ ;
CHITTATTU, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (14) :484-485
[6]   MODERN ORGANOSELENIUM CHEMISTRY [J].
CLIVE, DLJ .
TETRAHEDRON, 1978, 34 (08) :1049-1132
[7]   TOTAL SYNTHESIS OF (+/-)-5,6-OXIDO-7,9-TRANS,11,14-CIS-EICOSAPENTAENOIC ACID, A POSSIBLE PRECURSOR OF SRSA [J].
COREY, EJ ;
ARAI, Y ;
MIOSKOWSKI, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (22) :6748-6749
[8]   CHEMICAL AND ENZYMIC SYNTHESES OF 5-HPETE - KEY BIOLOGICAL PRECURSOR OF SLOW-REACTING SUBSTANCE OF ANAPHYLAXIS (SRS), AND 5-HETE [J].
COREY, EJ ;
ALBRIGHT, JO ;
BARTON, AE ;
HASHIMOTO, SI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (04) :1435-1436
[9]   SELECTIVE EPOXIDATION OF EICOSA-CIS-5,8,11,14-TETRAENOIC (ARACHIDONIC) ACID AND EICOSA-CIS-8,11,14-TRIENOIC ACID [J].
COREY, EJ ;
NIWA, H ;
FALCK, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (06) :1586-1587
[10]   SYNTHESIS OF THE SLOW REACTING SUBSTANCE OF ANAPHYLAXIS LEUKOTRIENE C-1 FROM ARACHIDONIC-ACID [J].
COREY, EJ ;
BARTON, AE ;
CLARK, DA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (12) :4278-4279