TOTAL SYNTHESIS OF THE ETHANOL-INDUCIBLE, PROINFLAMMATORY AUTACOID 3(S)-HYDROXY-LEUKOTRIENE B-4 (3-OH-LTB(4)) AND ANALOGS

被引：15

作者：

CHAUHAN, K

BHATT, RK

FALCK, JR

CAPDEVILA, JH

机构：

[1] UNIV TEXAS, SW MED CTR, DEPT MOLEC GENET, DALLAS, TX 75235 USA

[2] UNIV TEXAS, SW MED CTR, DEPT PHARMACOL, DALLAS, TX 75235 USA

[3] VANDERBILT UNIV, SCH MED, DEPT MED, NASHVILLE, TN 37205 USA

[4] VANDERBILT UNIV, SCH MED, DEPT BIOCHEM, NASHVILLE, TN 37205 USA

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 12期

关键词：

EICOSANOID; CHELATION-CONTROLLED REDUCTION; RIEKE ZINC; WITTIG;

D O I：

10.1016/S0040-4039(00)73170-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3(S)-Hydroxy-Leukotriene B-4 (1a), its 3(R)-epimer 1b, and a 14,15-acetylenic analogue were efficiently prepared via chelation-controlled reduction of ketone 12, obtained by acetylide addition to chiral beta-hydroxylactones 7/9.

引用

页码：1825 / 1828

页数：4

共 17 条

[1] THE USE OF RIEKE ZINC METAL IN THE SELECTIVE REDUCTION OF ALKYNES
CHOU, WN
CLARK, DL
WHITE, JB
[J]. TETRAHEDRON LETTERS, 1991, 32 (03) : 299 - 302
[2] DEOXY-SUGARS .6. THE CONSTITUTION OF BETA-METHYL-2-DEOXY-L-RIBOPYRANOSIDE AND OF ALPHA-BETA-METHYL-2-DEOXY-L-RIBOFURANOSIDE
DERIAZ, RE
OVEREND, WG
STACEY, M
WIGGINS, LF
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1949, (NOV): : 2836 - 2841
[3] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE
EVANS, DA
CHAPMAN, KT
CARREIRA, EM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) : 3560 - 3578
[4] HEPATIC-UPTAKE AND METABOLIC DISPOSITION OF LEUKOTRIENE-B4 IN RATS
HAGMANN, W
KORTE, M
[J]. BIOCHEMICAL JOURNAL, 1990, 267 (02) : 467 - 470
[5] A CHEMOENZYMATIC SYNTHESIS OF LEUKOTRIENE-B4
HAN, CQ
DITULLIO, D
WANG, YF
SIH, CJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (08) : 1253 - 1258
[6] HARPER TW, 1986, J BIOL CHEM, V261, P5414
[7] TOTAL SYNTHESIS OF LEUKOTRIENE-B(4)
KERDESKY, FAJ
SCHMIDT, SP
BROOKS, DW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (13) : 3516 - 3520
[8] GLYCOSYLIMIDATES .28. DIRECT 3,6-DI-O-PROTECTION OF GLUCAL AND GALACTAL
KINZY, W
SCHMIDT, RR
[J]. TETRAHEDRON LETTERS, 1987, 28 (18) : 1981 - 1984
[9] THE LEUKOTRIENES IN ALLERGY AND INFLAMMATION
MARX, JL
[J]. SCIENCE, 1982, 215 (4538) : 1380 - 1383
[10] MURPHY RC, COMMUNICATION

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