STUDIES DIRECTED TOWARDS THE TOTAL SYNTHESIS OF (+/-)-HIMBACINE

被引：16

作者：

DEBAECKE, G ^{[1
]}

DECLERCQ, PJ ^{[1
]}

机构：

[1] STATE UNIV GHENT,DEPT ORGAN CHEM,B-9000 GHENT,BELGIUM

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 41期

关键词：

D O I：

10.1016/0040-4039(95)01520-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of aldehyde 11a is reported based upon the intramolecular Diels-Alder reaction of triene 10, the butenolide-diene part of which was obtained in one step via the condensation of the enolate derived from the (Z)-enoate ester 5 with 2-acetoxypropanal. Aldehyde 11a possesses the correct stereochemistry of the tricyclic part of himbacine, an important muscarine receptor antagonist.

引用

页码：7515 / 7518

页数：4

共 20 条

[1] THE INTRAMOLECULAR DIELS-ALDER REACTION [J].

BRIEGER, G ;

BENNETT, JN .

CHEMICAL REVIEWS, 1980, 80 (01) :63-97

[2]

BROWN RFC, 1956, AUST J CHEM, V9, P283

[3]

Ciganek E., 1984, ORG REACT NY, V32, P1, DOI DOI 10.1002/0471264180.OR032.01

[4] SELECTIVE DEPROTECTION OF ALCOHOLIC AND PHENOLIC SILYL ETHERS [J].

COLLINGTON, EW ;

FINCH, H ;

SMITH, IJ .

TETRAHEDRON LETTERS, 1985, 26 (05) :681-684

[5]

Corey E. J., 1976, TETRAHEDRON LETT, V17, P7

[6] STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION [J].

CRAIG, D .

CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) :187-238

[7] THE INTRAMOLECULAR DIELS-ALDER REACTION - RECENT ADVANCES AND SYNTHETIC APPLICATIONS [J].

FALLIS, AG .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (02) :183-234

[8] DIRECT DETERMINATION OF MOLECULAR STRUCTURE - CRYSTAL STRUCTURE OF HIMBACINE HYDROBROMIDE AT - 150 DEGREES C [J].

FRIDRICHSONS, J ;

MATHIESON, AM .

ACTA CRYSTALLOGRAPHICA, 1962, 15 (FEB) :119-&

[9] PREPARATION OF (E)-ALPHA,BETA-UNSATURATED AROMATIC-ALDEHYDES BY HIGH STEREOSELECTIVE OLEFINFORMYLATION [J].

GAUDEMAR, M ;

BELLASSOUED, M .

TETRAHEDRON LETTERS, 1990, 31 (03) :349-352

[10] THE TAUTOMERISM OF A PHOSPHONO ENAMINE [J].

HIGHET, RJ ;

JONES, TH .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :4038-4040

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