Efficient synthesis of (R)- and (S)-3-octanol, (R)-2-dodecanol, (R)-2-methyl-4-heptanol and (R)-2-methyl-4-octanol:: the pheromones of Myrmica scabrinodis, Crematogaster castanea, C-liengmei, C-auberti and Metamasius hemipterus

被引:14
作者
Cho, BT [1 ]
Kim, DJ [1 ]
机构
[1] Hallym Univ, Dept Chem, Chunchon 200702, South Korea
关键词
chiral insect pheromone; asymmetric reduction; chiral beta-hydroxy sulfides; dianion alkylation;
D O I
10.1016/S0040-4020(03)00254-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient synthesis of optically active insect pheromones, such as (R)- and (S)-3-octanol, (R)-2-dodecanol, (R)-2-methyl-4-heptanol and (R)-2-methyl-4-octanol starting from non-racemic beta-hydroxy sulfides has been established. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2457 / 2462
页数:6
相关论文
共 35 条
[1]   Enantioselective synthesis of (R)- and (S)-2-methyl-4-octanol, the male-produced aggregation pheromone of Curculionidae species [J].
Baraldi, PT ;
Zarbin, PHG ;
Vieira, PC ;
Corrêa, AG .
TETRAHEDRON-ASYMMETRY, 2002, 13 (06) :621-624
[3]   THE PHEROMONAL ACTIVITY OF CHIRAL 3-OCTANOL FOR MYRMICA ANTS [J].
CAMMAERTS, MC ;
ATTYGALLE, AB ;
EVERSHED, RP ;
MORGAN, ED .
PHYSIOLOGICAL ENTOMOLOGY, 1985, 10 (01) :33-36
[4]   BEHAVIORAL ACTIVITY OF PURE CHIRAL 3-OCTANOL FOR THE ANTS MYRMICA-SCABRINODIS NYL AND MYRMICA-RUBRA L [J].
CAMMAERTS, MC ;
MORI, K .
PHYSIOLOGICAL ENTOMOLOGY, 1987, 12 (04) :381-385
[5]   Highly efficient synthesis of chiral β-hydroxy sulfides with high enantiomeric purity via CBS-oxazaborolidine-catalyzed borane reduction [J].
Cho, BT ;
Choi, OK ;
Kim, DJ .
TETRAHEDRON-ASYMMETRY, 2002, 13 (07) :697-703
[6]  
CHO BT, ACS S SERIES, V783
[7]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO
[8]  
2-Z
[9]   Enantioselective reductions by chirally modified alumino- and borohydrides [J].
Daverio, P ;
Zanda, M .
TETRAHEDRON-ASYMMETRY, 2001, 12 (16) :2225-2259
[10]   PHEROMONE SYNTHESIS .90. SYNTHESIS OF BOTH THE ENANTIOMERS OF 3-OCTANOL, THE PHEROMONE OF VARIOUS SPECIES OF ANTS [J].
FUJIWHARA, M ;
MORI, K .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1986, 50 (11) :2925-2927