TOTAL SYNTHESIS OF (+)-LEUKOTRIENE B4 METHYL-ESTER AND ITS 5-EPIMER FROM (R)-GLYCIDOL

被引：29

作者：

AVIGNONTROPIS, M

TREILHOU, M

POUGNY, JR

FRECHARDORTUNO, I

LINSTRUMELLE, G

机构：

[1] CNRS,CTR RECH BIOCHIM & GENET CELLULAIRES,F-31062 TOULOUSE,FRANCE

[2] ECOLE NORMALE SUPER,CHIM LAB,F-75231 PARIS 05,FRANCE

来源：

TETRAHEDRON | 1991年 / 47卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(01)89730-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Pd-Cu coupling reaction of a chiral hydroxy-(E,E)-iododiene with a racemic acetylenic alcohol followed by reduction of the dienyne leads to the desired (Z,E,E) geometry and allows synthesis of LTB4 and its 5-epimer after separation of diastereomers.

引用

页码：7279 / 7286

页数：8

共 27 条

[1] AN EFFICIENT SYNTHESIS OF LEUKOTRIENE-B4
AVIGNONTROPIS, M
TREILHOU, M
LEBRETON, J
POUGNY, JR
FRECHARDORTUNO, I
HUYNH, C
LINSTRUMELLE, G
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[2] IMPROVED STEREOSELECTIVE REDUCTION OF A E,E, CONJUGATED DIENYNE TO A E,E,Z CONJUGATED TRIENE
AVIGNONTROPIS, M
POUGNY, JR
[J]. TETRAHEDRON LETTERS, 1989, 30 (37) : 4951 - 4952
[3] IMPROVED HIGHLY EFFICIENT SYNTHESIS OF ALPHA,BETA-ACETYLENIC KETONES - NATURE OF THE INTERMEDIATE FROM THE REACTION OF LITHIUM ACETYLIDE WITH BORON-TRIFLUORIDE ETHERATE
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[4] PROTON MAGNETIC-RESONANCE SPECTRA OF LEUKOTRIENE-A METHYL ESTER(I), LEUKOTRIENE-B METHYL-ESTER DIACETATE(II) AND 12-EPI-6-E,8-Z-LEUKOTRIENE-B METHYL-ESTER DIACETATE(III,5-S,12-S-DI-HETE)
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[5] LEUKOTRIENE-B - TOTAL SYNTHESIS AND ASSIGNMENT OF STEREOCHEMISTRY
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[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (27) : 7984 - 7985
[6] A STEREOCONTROLLED AND EFFECTIVE SYNTHESIS OF LEUKOTRIENE-B-(1)
COREY, EJ
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KIM, KS
HOPKINS, PB
BRION, F
[J]. TETRAHEDRON LETTERS, 1981, 22 (12) : 1077 - 1080
[7] STEREOSELECTIVE SYNTHESIS OF POLYENIC ALCOHOLS - A NEW ROUTE TO THE LEUKOTRIENES-B
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LINSTRUMELLE, G
[J]. TETRAHEDRON LETTERS, 1986, 27 (48) : 5857 - 5860
[8] STEREOSPECIFIC SYNTHESIS OF LEUKOTRIENE B4 (LTB4)
GUINDON, Y
ZAMBONI, R
LAU, CK
ROKACH, J
[J]. TETRAHEDRON LETTERS, 1982, 23 (07) : 739 - 742
[9] TOTAL SYNTHESIS OF LTB4 AND ANALOGS
GUINDON, Y
DELORME, D
LAU, CK
ZAMBONI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (02) : 267 - 275
[10] A CHEMOENZYMATIC SYNTHESIS OF LEUKOTRIENE-B4
HAN, CQ
DITULLIO, D
WANG, YF
SIH, CJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (08) : 1253 - 1258

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