A general synthesis of (2Z)-terpenoic acids

被引：10

作者：

Cahard, D ^{[1
]}

Mammeri, M ^{[1
]}

Poirier, JM ^{[1
]}

Duhamel, L ^{[1
]}

机构：

[1] Univ Rouen, CNRS, Inst Rech Chim Organ Fine, F-76821 Mt St Aignan, France

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 19期

关键词：

enolates; oxidation; stereocontrol; retinoids; terpenes and terpenoids;

D O I：

10.1016/S0040-4039(00)00457-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A three-step synthesis of (2Z), (4E)-polyenic acids 6 is described. Condensation of aldehydes 1 with potassium prenal enolate led to dihydropyranols 3 which were oxidized into dihydropyrones 5, precursors of (2Z), (4E)-polyenic acids 6. The procedure was applied to a synthesis of 13-cis-retinoic acids from beta-ionylidene acetaldehydes. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3619 / 3622

页数：4

共 22 条

[1] THE REFORMATSKY REACTION .2. PREPARATION OF ORGANOZINC COMPOUNDS, USING THE BROMOZIC SALT DERIVED FROM GAMMA-BROMOSENECIOIC ACID, AS WELL AS A STUDY OF THEIR REACTIVITY [J].

BELLASSOUED, M ;

HABBACHI, F ;

GAUDEMAR, M .

TETRAHEDRON, 1987, 43 (08) :1785-1792

[2]

BESTMAN HJ, 1983, Patent No. 3200231

[3]

BOUTWELL RK, 1979, ONCOLOGY OVERVIEW SE

[4]

Cahard D, 1998, SYNLETT, P1399

[5] Regioselective addition of the prenal potassium dienolate onto α,β-unsaturated aldehydes.: A short access to polyenaldehydes. [J].

Cahard, D ;

Poirier, JM ;

Duhamel, P .

TETRAHEDRON LETTERS, 1998, 39 (39) :7093-7096

[6] SYNTHESIS OF COMPOUNDS CONTAINING ISOPRENE UNIT - CONDENSATION OF 3-METHYLBUT-3-ENOIC AND 3-METHYLBUT-2-ENOIC ACIDS WITH CARBONYL-COMPOUNDS [J].

CAINELLI, G ;

CARDILLO, G ;

CONTENTO, M ;

TRAPANI, G ;

RONCHI, AU .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (04) :400-404

[7] SOME ASPECTS OF THE STEREOSPECIFIC SYNTHESIS OF TERPENOIDS BY MEANS OF ISOPRENE UNITS [J].

CAINELLI, G ;

CARDILLO, G .

ACCOUNTS OF CHEMICAL RESEARCH, 1981, 14 (03) :89-94

[8] SYNTHESIS OF COMPOUNDS CONTAINING THE ISOPRENE UNIT - STEREOSPECIFIC SYNTHESIS OF BETA-IONILIDENEACETIC ACID AND DEHYDRO-BETA-IONILIDENEACETIC ACID, A KEY INTERMEDIATE TO ABSCISIC-ACID [J].

CAINELLI, G ;

CARDILLO, G ;

ORENA, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06) :1597-1599

[9]

CAINELLI G, 1973, GAZZ CHIM ITAL, V103, P117

[10] SYNTHESIS OF COMPOUNDS CONTAINING ISOPRENE UNIT - STEREOSPECIFIC SYNTHESIS OF DEHYDRONEROL ISOVALERATE - COMPONENT OF ANTHEMIS-MONTANA L [J].

CARDILLO, G ;

ORENA, M ;

SANDRI, S .

TETRAHEDRON, 1976, 32 (01) :107-108

← 1 2 3 →