Trends in chrysanthemic acid chemistry: A survey of recent pyrethrum syntheses

被引：17

作者：

Jeanmart, S ^{[1
]}

机构：

[1] Fac Univ Notre Dame Paix, B-5000 Namur, Belgium

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2003年 / 56卷 / 06期

关键词：

D O I：

10.1071/CH02216

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An overview is given of the recent trends in the field of chrysanthemic acid synthesis. To show the scope of organic chemistry involved, pyrethrum chemistry is presented in terms of the reactions employed in total synthesis of chrysantemic acid, with a strong emphasis on construction of the cyclopropane moiety. The various methodologies are classified into two main groups: ylide, carbenoid chemistry, and other related additions; and 1,3-elimination and related isomerization of 2,2-dimethyldimedone.

引用

收藏

页码：559 / 566

页数：8

相关论文

共 52 条

[1] Highly enantioselective synthesis of chiral imides and derived products via chiral base desymmetrisation [J].

Adams, DJ ;

Blake, AJ ;

Cooke, PA ;

Gill, CD ;

Simpkins, NS .

TETRAHEDRON, 2002, 58 (23) :4603-4615

[2] CATALYTIC ASYMMETRIC-SYNTHESIS OF CYCLOPROPANE-CARBOXYLIC ACIDS - AN APPLICATION OF CHIRAL COPPER CARBENOID REACTION [J].

ARATANI, T .

PURE AND APPLIED CHEMISTRY, 1985, 57 (12) :1839-1844

[3] ASYMMETRIC-SYNTHESIS OF PERMETHRIC ACID - STEREOCHEMISTRY OF CHIRAL COPPER CARBENOID REACTION [J].

ARATANI, T ;

YONEYOSHI, Y ;

NAGASE, T .

TETRAHEDRON LETTERS, 1982, 23 (06) :685-688

[4]

ARATANI T, 1975, TETRAHEDRON LETT, V16, P1707

[5]

ARATANI T, 1977, TETRAHEDRON LETT, V18, P2599

[6] SYNTHESES OF PYRETHROID ACIDS [J].

ARLT, D ;

JAUTELAT, M ;

LANTZSCH, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (09) :703-722

[7] Cis-selective asymmetric cyclopropanation of olefins catalyzed by five-coordinate [RuCl(PNNP)]+ complexes [J].

Bachmann, S ;

Furler, M ;

Mezzetti, A .

ORGANOMETALLICS, 2001, 20 (10) :2102-2108

[8] Chemoenzymatic routes to chiral (non-racemic) cyclopropanes. Preparation of a key intermediate for the synthesis of (1R)-cis-pyrethroids [J].

Banwell, MG ;

Forman, GS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (21) :2565-2566

[9] X-RAY ANALYSIS OF SYNTHETIC (4S)-2-(PROP-2-ENYL)RETHRON-4-YL (1R,3R)-CHRYSANTHEMATE "6-BROMO-2,4-DINITROPHENYLHYDRAZONE, AND CHIROPTICAL CORRELATION WITH 6 NATURAL PYRETHRIN ESTERS [J].

BEGLEY, MJ ;

CROMBIE, L ;

SIMMONDS, DJ ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (11) :1230-1235

[10] NUCLEAR MAGNETIC RESONANCE SPECTRA OF NATURAL PYRETHRINS AND RELATED COMPOUNDS [J].

BRAMWELL, AF ;

CROMBIE, L ;

HEMESLEY, P ;

PATTENDEN, G ;

ELLIOTT, M ;

JANES, NF .

TETRAHEDRON, 1969, 25 (08) :1727-+

← 1 2 3 4 5 6 →