Practical route to a new class of LTD(4) receptor antagonists

被引：247

作者：

Larsen, RD ^{[1
]}

Corley, EG ^{[1
]}

King, AO ^{[1
]}

Carroll, JD ^{[1
]}

Davis, P ^{[1
]}

Verhoeven, TR ^{[1
]}

Reider, PJ ^{[1
]}

Labelle, M ^{[1
]}

Gauthier, JY ^{[1
]}

Xiang, YB ^{[1
]}

Zamboni, RJ ^{[1
]}

机构：

[1] MERCK & CO INC,MERCK FROSST CTR THERAPEUT RES,POINTE CLAIRE,PQ H9R 4P8,CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 10期

关键词：

D O I：

10.1021/jo952103j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general approach to the synthesis of a new class of LTD(4) antagonists is presented. The key diarylpropane framework was prepared by Claisen-Schmidt condensation and selective reduction of the enone. Depending on the bridge to the 7-chloroquinaldine moiety, alkylation or Heck coupling methodology was developed. The chiral sulfides were introduced by asymmetric reduction of the diarylpropanone intermediates and subsequent inversion of the chiral center.

引用

页码：3398 / 3405

页数：8

共 45 条

[1] RULES FOR RING-CLOSURE - RING FORMATION BY CONJUGATE ADDITION OF OXYGEN NUCLEOPHILES [J].

BALDWIN, JE ;

THOMAS, RC ;

KRUSE, LI ;

SILBERMAN, L .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (24) :3846-3852

[2] ORTHO METALATIONS - ADVANTAGE OF THE AMIDE FUNCTIONS [J].

BEAK, P ;

BROWN, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (24) :4463-4464

[3] ORTHO LITHIATION OF TERTIARY BENZAMIDES [J].

BEAK, P ;

BROWN, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (10) :1823-1824

[4] THE TERTIARY AMIDE AS AN EFFECTIVE DIRECTOR OF ORTHO LITHIATION [J].

BEAK, P ;

BROWN, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (01) :34-46

[5]

BINIECKI S, 1958, Ann Pharm Fr, V16, P21

[6] SYNTHESIS OF 3,3A-DIHYDRO-8H-PYRAZOLO[5,1-A]ISOINDOL-8-ONES AND 8H-PYRAZOLO[5,1-A]ISOINDOL-8-ONES [J].

BOUSQUET, EW ;

MORAN, MD ;

HARMON, J ;

JOHNSON, AL ;

SUMMERS, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (15) :2208-2211

[7] THE INSITU PROTECTION OF ALDEHYDES VIA ALPHA-AMINO ALKOXIDES [J].

COMINS, DL ;

BROWN, JD .

TETRAHEDRON LETTERS, 1981, 22 (42) :4213-4216

[8] A ONE-POT ORTHO-ALKYLATION OF AROMATIC-ALDEHYDES [J].

COMINS, DL ;

BROWN, JD ;

MANTLO, NB .

TETRAHEDRON LETTERS, 1982, 23 (39) :3979-3982

[9] ORTHO METALATION DIRECTED BY ALPHA-AMINO ALKOXIDES [J].

COMINS, DL ;

BROWN, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (06) :1078-1083

[10] LITHIATION OF HETEROCYCLES DIRECTED BY ALPHA-AMINO ALKOXIDES [J].

COMINS, DL ;

KILLPACK, MO .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (01) :104-109

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