NEW TRIENE SYNTHESIS FROM SORBIC ACID - 2-STEP SYNTHESIS OF CIS-GALBANOLENES AND TRANS-GALBANOLENES

被引：6

作者：

FEHR, C

GALINDO, J

CHAPPUIS, S

机构：

[1] Firmenich SA, Research Laboratories, CH-1211 Geneva 8

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 18期

关键词：

SORBIC ACID; ALDOL REACTION; TRIENE SYNTHESIS; OLEFINATION; DECARBOXYLATIVE ELIMINATION;

D O I：

10.1016/S0040-4039(00)92216-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lithium dianion of sorbic acid reacts with hexanal at the C(2)-position to afford separable anti- and syn-hydroxy carboxylic acids 3 and 4 (87%; 3/4 = 59:41 or 79%; 3/4 = 16:84), whose stereospecific anti-decarboxylative elimination respectively affords (3E, 5Z)- and (3E, 5E)-1,3,5-undecatriene (1) and (2) (cis- and trans-galbanolenes (1) and (2) (69%). An alternative route to 1 involves conversion of 3, 4 to cis-lactone 7 (45% after chromatography) followed by thermal syn-decarboxylation (81%). The described procedure is both new and of general applicability, as illustrated by the synthesis of trienes with different substitution pattern.

引用

收藏

页码：2465 / 2468

页数：4

相关论文

共 51 条

[1] STEREOSPECIFIC INTRODUCTION OF DOUBLE-BONDS VIA THERMOLYSIS OF BETA-LACTONES [J].

ADAM, W ;

BAEZA, J ;

LIU, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (06) :2000-&

[2] SYNTHESIS OF PHENYL ENOL ETHERS VIA DECARBOXYLATION OF BETA-LACTONES DERIVED FROM LITHIUM ALPHA-PHENOXY-ALPHA-LITHIOACETATE SYNTHON [J].

ADAM, W ;

FICK, HH .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (24) :4574-4577

[3] HIGHLY STEREOSELECTIVE AND REGIOSELECTIVE PALLADIUM-CATALYZED SYNTHESES OF (3E,5Z)-UNDECATRIENE, (3E,5E)-UNDECATRIENE, AND (3Z,5E)-1,3,5-UNDECATRIENE [J].

ANDREINI, BP ;

BENETTI, M ;

CARPITA, A ;

ROSSI, R .

TETRAHEDRON, 1987, 43 (20) :4591-4600

[4] UNSATURATED CARBOXYLIC-ACID POLYENOLATES - LITHIUM TRIENOLATE OF SORBIC ACID AS A D6 SYNTHON - ADDITION TO KETONES AND UNSATURATED-KETONES [J].

BALLESTER, P ;

COSTA, A ;

GARCIARASO, A ;

MESTRES, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (10) :2797-2803

[5] LITHIUM TRIENOLATE OF SORBIC ACID AS A D6 SYNTHON - SYNTHESIS OF 7-HYDROXY 2,4-DIENOIC ACIDS [J].

BALLESTER, P ;

COSTA, A ;

GARCIARASO, A ;

GOMEZSOLIVELLAS, A ;

MESTRES, R .

TETRAHEDRON LETTERS, 1985, 26 (30) :3625-3628

[6] A NOVEL STEREOSELECTIVE SYNTHESIS OF 1,3,5-TRIENES VIA SO2 EXTRUSION FROM SULFOLENES [J].

BLOCH, R ;

BENECOU, C ;

GUIBEJAMPEL, E .

TETRAHEDRON LETTERS, 1985, 26 (10) :1301-1304

[7] ALPHA-HALOALKANESULFONYL BROMIDES IN ORGANIC-SYNTHESIS .5. VERSATILE REAGENTS FOR THE SYNTHESIS OF CONJUGATED POLYENES, ENONES, AND 1,3-OXATHIOLE 1,1-DIOXIDES [J].

BLOCK, E ;

ASLAM, M ;

ESWARAKRISHNAN, V ;

GEBREYES, K ;

HUTCHINSON, J ;

IYER, R ;

LAFFITTE, JA ;

WALL, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4568-4580

[8] STEREOSPECIFIC SYNTHESES AND SPECTROSCOPIC PROPERTIES OF ISOMERIC 2,4,6,8-UNDECATETRAENES - NEW HYDROCARBONS FROM THE MARINE BROWN ALGA-GIFFORDIA-MITCHELLAE .4. [J].

BOLAND, W ;

SIELER, C ;

FEIGEL, M .

HELVETICA CHIMICA ACTA, 1987, 70 (04) :1025-1040

[9]

CHAPUIS C, UNPUB TETRAHEDRON LE

[10]

CHRETIEN.Y, 1967, B SOC CHIM FR, P97

← 1 2 3 4 5 6 →