REACTIVITY OF TRICARBONYL(PENTADIENYL)IRON(1+) CATIONS - ENANTIOSELECTIVE SYNTHESIS OF 5-HETE METHYL-ESTER

被引：69

作者：

TAO, CL ^{[1
]}

DONALDSON, WA ^{[1
]}

机构：

[1] MARQUETTE UNIV,DEPT CHEM,MILWAUKEE,WI 53233

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 08期

关键词：

D O I：

10.1021/jo00060a033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of racemic 5-HETE methyl ester (1) and of 5-HETE lactone (5-HL) were accomplished in 11 steps from tricarbonyl [1-(methoxycarbonyl)pentadienyl]iron(1+) hexafluorophosphate (2). A second synthesis of 1 from 2 in five steps was also achieved. Starting with optically active 5 the synthesis of (+)-1 and(-)-1 in high optical purity was realized. The stereochemistry of the 6,8-diene portion and the stereochemistry of the C5 asymmetric center of 1 were controlled by the (tricarbonyl)iron adjunct.

引用

收藏

页码：2134 / 2143

页数：10

相关论文

共 51 条

[1] PHENYLSELENYLATION OF ARACHIDONIC-ACID AS A ROUTE TO INTERMEDIATES FOR LEUKOTRIENE SYNTHESIS - ISOMERIZATION OF CONJUGATED DIENES DURING SELENOXIDE ELIMINATION [J].

BALDWIN, JE ;

REED, NV ;

THOMAS, EJ .

TETRAHEDRON, 1981, 37 :263-267

[2] A NEW STEREOSELECTIVE SYNTHESIS OF (E,Z)-CONJUGATED HYDROXY-DIENES, KEY INTERMEDIATES FOR THE SYNTHESIS OF HETES [J].

BLOCH, R ;

GASPARINI, G ;

GIRARD, C .

CHEMISTRY LETTERS, 1988, (11) :1927-1930

[3]

BORGEAT P, 1976, J BIOL CHEM, V251, P7816

[4]

BORGEAT P, 1976, J BIOL CHEM, V252, P8772

[5] SIMPLIFIED, ONE-POT PROCEDURE FOR THE SYNTHESIS OF [(PH3P)CUH]6, A STABLE COPPER HYDRIDE FOR CONJUGATE REDUCTIONS [J].

BRESTENSKY, DM ;

HUSELAND, DE ;

MCGETTIGAN, C ;

STRYKER, JM .

TETRAHEDRON LETTERS, 1988, 29 (31) :3749-3752

[6] CONFORMATIONAL ANALYSIS OF TRICARBONYL(DIENE)IRON COMPOUNDS [J].

CLINTON, NA ;

LILLYA, CP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (10) :3058-&

[7] 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

[8] A NEW GENERAL SYNTHETIC ROUTE TO BRIDGED CARBOXYLIC ORTHO ESTERS [J].

COREY, EJ ;

RAJU, N .

TETRAHEDRON LETTERS, 1983, 24 (50) :5571-5574

[9] A PRACTICAL PROCESS FOR LARGE-SCALE SYNTHESIS OF (S)-5-HYDROXY-6-TRANS-8,11,14-CIS-EICOSATETRAENOIC ACID (5-HETE) [J].

COREY, EJ ;

HASHIMOTO, SI .

TETRAHEDRON LETTERS, 1981, 22 (04) :299-302

[10]

Danishefsky S. J., 1986, ALDRICHIM ACTA, V19, P59

← 1 2 3 4 5 6 →