Stereocontrolled synthesis of (E,E,E)-chlorotrienes: Efficient intermediates for the construction of all E conjugated polyenes

被引：22

作者：

Crousse, B ^{[1
]}

Alami, M ^{[1
]}

Linstrumelle, G ^{[1
]}

机构：

[1] ECOLE NORMALE SUPER,DEPT CHIM,CNRS,F-75231 PARIS 05,FRANCE

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(97)01156-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective reduction of conjugated homopropargylic alcohols 1 followed by an elimination reaction, allows an efficient approach to stereodefined (E,E,E)-chlorotrienes. The interest of these chlorotrienes was illustrated by a stereocontrolled synthesis of navenone B and all E conjugated polyenes (trienes, tetraenes and hexaenes). (C) 1997 Published by Elsevier Science Ltd.

引用

页码：5297 / 5300

页数：4

共 43 条

[1]

ALAMI M, 1993, SYNLETT, P217

[2] AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL CHLORIDES WITH TERMINAL ACETYLENES [J].

ALAMI, M ;

LINSTRUMELLE, G .

TETRAHEDRON LETTERS, 1991, 32 (43) :6109-6112

[3] AN EFFICIENT SYNTHESIS OF 1,3(E),5(Z), 1,3(E),5(E) AND 1,3(Z),5(Z)-TRIENES - APPLICATION TO THE SYNTHESIS OF GALBANOLENES AND (9Z,11E)-9,11,13-TETRADECATRIEN-1-YL ACETATE [J].

ALAMI, M ;

GUEUGNOT, S ;

DOMINGUES, E ;

LINSTRUMELLE, G .

TETRAHEDRON, 1995, 51 (04) :1209-1220

[4] The first total synthesis of a member of the manumycin family of antibiotics: Alisamycin [J].

Alcaraz, L ;

Macdonald, G ;

Kapfer, I ;

Lewis, NJ ;

Taylor, RJK .

TETRAHEDRON LETTERS, 1996, 37 (36) :6619-6622

[5] TOTAL SYNTHESIS OF (+)-LEUKOTRIENE B4 METHYL-ESTER AND ITS 5-EPIMER FROM (R)-GLYCIDOL [J].

AVIGNONTROPIS, M ;

TREILHOU, M ;

POUGNY, JR ;

FRECHARDORTUNO, I ;

LINSTRUMELLE, G .

TETRAHEDRON, 1991, 47 (35) :7279-7286

[6] A NEW STRAIGHTFORWARD AND GENERAL-APPROACH TO DIENAMIDE NATURAL-PRODUCTS [J].

BABUDRI, F ;

FIANDANESE, V ;

NASO, F ;

PUNZI, A .

TETRAHEDRON LETTERS, 1994, 35 (13) :2067-2070

[7] A GENERAL-APPROACH TO CONJUGATED (E,E)-DIENES THROUGH SEQUENTIAL COUPLING REACTIONS [J].

BABUDRI, F ;

FIANDANESE, V ;

MAZZONE, L ;

NASO, F .

TETRAHEDRON LETTERS, 1994, 35 (47) :8847-8850

[8]

Cahiez G, 1995, ENCY REAGENTS ORGANI, P3229

[9] A new stereocontrolled, pyrylium-based route to conjugated dienynes: The first synthesis of Carduusyne A [J].

Charoenying, P ;

Davies, H ;

McKerrecher, D ;

Taylor, RJK .

TETRAHEDRON LETTERS, 1996, 37 (11) :1913-1916

[10] PALLADIUM-CATALYZED REACTION OF (E)-DICHLOROETHENE AND (Z)-DICHLOROETHENE WITH 1-ALKYNES - AN EFFICIENT STEREOSPECIFIC SYNTHESIS OF (E)-ENEDIYNES AND (Z)-ENEDIYNES [J].

CHEMIN, D ;

LINSTRUMELLE, G .

TETRAHEDRON, 1994, 50 (18) :5335-5344

← 1 2 3 4 5 →