Chiral acetals: Stereocontrolled syntheses of 16-, 17-, and 18-hydroxyeicosatetraenoic acids, cytochrome P-450 arachidonate metabolites

被引：20

作者：

Heckmann, B

Mioskowski, C

Lumin, S

Falck, JR

Wei, SZ

Capdevila, JH

机构：

[1] UNIV STRASBOURG 1,LAB SYNTH BIOORGAN,CNRS,F-67401 ILLKIRCH GRAFFENS,FRANCE

[2] UNIV TEXAS,SW MED CTR,DEPT MOL GENET & PHARMACOL,DALLAS,TX 75235

[3] VANDERBILT UNIV,MED CTR,DEPT MED,NASHVILLE,TN 37232

[4] VANDERBILT UNIV,MED CTR,DEPT BIOCHEM,NASHVILLE,TN 37232

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 09期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(96)00059-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral adducts from Grignard or allylsilane additions to 1,3-dioxan/1,3-dioxolan-4-ones were exploited for the total synthesis of the R- and S-isomers of the title eicosanoids.

引用

页码：1425 / 1428

页数：4

共 13 条

[1]

CAPDEVILA JH, 1990, J BIOL CHEM, V265, P10865

[2] CYTOCHROME-P450 AND THE ARACHIDONATE CASCADE [J].

CAPDEVILA, JH ;

FALCK, JR ;

ESTABROOK, RW .

FASEB JOURNAL, 1992, 6 (02) :731-736

[3]

CARROLL MS, COMMUNICATION

[4] GAS-CHROMATOGRAPHIC MASS-SPECTROMETRIC CHARACTERIZATION OF SOME NOVEL HYDROXYEICOSATETRAENOIC ACIDS FORMED ON INCUBATION OF ARACHIDONIC-ACID WITH MICROSOMES FROM INDUCED RAT LIVERS [J].

CLARE, RA ;

HUANG, S ;

DOIG, MV ;

GIBSON, GG .

JOURNAL OF CHROMATOGRAPHY-BIOMEDICAL APPLICATIONS, 1991, 562 (1-2) :237-247

[5]

FALCK JR, 1990, J BIOL CHEM, V265, P10244

[6] ENANTIOSPECIFIC SYNTHESIS OF 17-HYDROXYEICOSATETRAENOIC AND 18-HYDROXYEICOSATETRAENOIC ACIDS, CYTOCHROME-P450 ARACHIDONATE METABOLITES [J].

FALCK, JR ;

LUMIN, S ;

LEE, SG ;

HECKMANN, B ;

MIOSKOWSKI, C ;

KARARA, A ;

CAPDEVILA, J .

TETRAHEDRON LETTERS, 1992, 33 (34) :4893-4896

[7] NUCLEOPHILIC-SUBSTITUTION AT THE ACETALIC CENTER OF MANDELATE 1,3-DIOXOLAN-4-ONES USING MAGNESIO-COPPER REAGENTS - APPLICATION TO THE SYNTHESIS OF CHIRAL SECONDARY ALCOHOLS [J].

HECKMANN, B ;

MIOSKOWSKI, C ;

YU, JR ;

FALCK, JR .

TETRAHEDRON LETTERS, 1992, 33 (36) :5201-5204

[8] OXIDATIVE DECARBOXYLATION OF MANDELATE ETHERS AND ALPHA-SUBSTITUTED PHENYLACETATES VIA DIOXETANONE GENERATION [J].

HECKMANN, B ;

ALAYRAC, C ;

MIOSKOWSKI, C ;

CHANDRASEKHAR, S ;

FALCK, JR .

TETRAHEDRON LETTERS, 1992, 33 (36) :5205-5208

[9]

LAETHEM RM, 1993, J BIOL CHEM, V268, P12912

[10] UBER DIE REAKTION VON TERTIAREN VINYLCARBINOLEN MIT VINYLATHERN - EINE NEUE METHODE ZUR HERSTELLUNG VON GAMMA DELTA-UNGESATTIGTEN ALDEHYDEN [J].

MARBET, R ;

SAUCY, G .

HELVETICA CHIMICA ACTA, 1967, 50 (07) :2095-&

← 1 2 →