INSECT PHEROMONE SYNTHESIS USING MN-SALEN CATALYZED ASYMMETRIC EPOXIDATION AS A KEY STEP

被引:34
作者
HAMADA, T [1 ]
DAIKAI, K [1 ]
IRIE, R [1 ]
KATSUKI, T [1 ]
机构
[1] KYUSHU UNIV 33,FAC SCI,DEPT CHEM,HIGASHI KU,FUKUOKA 81281,JAPAN
关键词
D O I
10.1016/0957-4166(95)00319-K
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantioselective synthesis of three insect pheromones, (5Z, 13S)-5-tetradecen-13-olide, (9R)-decan-9-olide, and (S)-2-acetoxytridecane, has been achieved by using Mn-salen catalyzed asymmetric epoxidation as a key step.
引用
收藏
页码:2441 / 2451
页数:11
相关论文
共 18 条
[1]   AGGREGATION PHEROMONE COMPONENTS IN DROSOPHILA-MULLERI - A CHIRAL ESTER AND AN UNSATURATED KETONE [J].
BARTELT, RJ ;
SCHANER, AM ;
JACKSON, LL .
JOURNAL OF CHEMICAL ECOLOGY, 1989, 15 (01) :399-411
[2]   EXCEPTIONALLY EASY ISOMERIZATION OF ACETYLENIC ALCOHOLS WITH POTASSIUM 3-AMINOPROPYLAMIDE - NEW, HIGH-YIELD SYNTHESIS OF FUNCTIONALLY DIFFERENTIATED ALPHA-OMEGA-DIFUNCTIONAL STRUCTURES [J].
BROWN, CA ;
YAMASHITA, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (23) :959-960
[3]   P-2-NICKEL CATALYST WITH ETHYLENEDIAMINE, A NOVEL SYSTEM FOR HIGHLY STEREOSPECIFIC REDUCTION OF ALKYNES TO CIS-OLEFINS [J].
BROWN, CA ;
AHUJA, VK .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (15) :553-554
[4]  
ENDERS D, 1991, LIEBIGS ANN CHEM, P1241
[5]  
FUKUDA T, 1995, SYNLETT, P197
[6]  
HAMADA T, 1995, SYNLETT, P407
[7]   RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].
INANAGA, J ;
HIRATA, K ;
SAEKI, H ;
KATSUKI, T ;
YAMAGUCHI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993
[8]   CATALYTIC ENANTIOSELECTIVE MACROLIDE SYNTHESIS .2. USE OF DIFFERENTIAL DEPROTECTION PROTOCOLS [J].
JONES, GB ;
CHAPMAN, BJ ;
HUBER, RS ;
BEATY, R .
TETRAHEDRON-ASYMMETRY, 1994, 5 (07) :1199-1202
[9]   THE SYNTHESIS OF MACRO-CYCLIC AND MEDIUM CYCLIC-COMPOUNDS .2. THE SYNTHESIS AND THE ABSOLUTE-CONFIGURATION OF PHORACANTHOLIDE-I AND PHORACANTHOLIDE-J - THE DEFENSIVE SECRETION OF THE EUCARYPT LONGICORN, PHORACANTHA-SYNONYMA [J].
KITAHARA, T ;
KOSEKI, K ;
MORI, K .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1983, 47 (02) :389-393
[10]   MODEL STUDIES FOR THE SYNTHESIS OF QUASSINOIDS .1. CONSTRUCTION OF THE BCE RING-SYSTEM [J].
KRAUS, GA ;
TASCHNER, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (06) :1175-1176