Easy Access to (E)-β-Ocimene

被引:15
作者
Yildizhan, Selma [1 ]
Schulz, Stefan [1 ]
机构
[1] TU Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany
关键词
terpenoids; Grignard reaction; alkenes; hydrocarbons; coupling; INSECT HERBIVORY; MECHANISM; ALCOHOLS;
D O I
10.1055/s-0031-1289869
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta-Ocimene is one of the most common monoterpenes found in Nature, but a simple and reliable synthesis of the pure E-isomer has been missing. Here, we report a simple procedure involving a Grignard coupling as the key step that allows its synthesis on gram scales. The configuration of the double bond is fixed in the starting material.
引用
收藏
页码:2831 / 2833
页数:3
相关论文
共 23 条
[1]   Identification of semiochemicals released during aphid feeding that attract parasitoid Aphidius ervi [J].
Du, YJ ;
Poppy, GM ;
Powell, W ;
Pickett, JA ;
Wadhams, LJ ;
Woodcock, CM .
JOURNAL OF CHEMICAL ECOLOGY, 1998, 24 (08) :1355-1368
[2]  
Honda K, 2010, COMPREHENSIVE NATURAL PRODUCTS II: CHEMISTRY AND BIOLOGY, VOL 4: CHEMICAL ECOLOGY, P563
[3]   VOLATILE GLANDULAR SECRETIONS OF 3 SPECIES OF NEW-WORLD ARMY ANTS, ECITON-BURCHELLI, LABIDUS-COECUS, AND LABIDUS-PRAEDATOR [J].
KEEGANS, SJ ;
BILLEN, J ;
MORGAN, ED ;
GOKCEN, OA .
JOURNAL OF CHEMICAL ECOLOGY, 1993, 19 (11) :2705-2719
[4]   EVIDENCE FOR A CYCLIC MECHANISM IN (ETA(3)-ALLYL)PALLADIUM CHEMISTRY - PROMOTION OF BETA-HYDRIDE ELIMINATION BY UNSATURATED ORGANOMETALLICS [J].
KEINAN, E ;
KUMAR, S ;
DANGUR, V ;
VAYA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) :11151-11152
[5]   Making sense of nectar scents:: the effects of nectar secondary metabolites on floral visitors of Nicotiana attenuata [J].
Kessler, Danny ;
Baldwin, Ian T. .
PLANT JOURNAL, 2007, 49 (05) :840-854
[6]   Chemical ecology and conservation biological control [J].
Khan, Zeyaur R. ;
James, David G. ;
Midega, Charles A. O. ;
Pickett, John A. .
BIOLOGICAL CONTROL, 2008, 45 (02) :210-224
[7]  
Knudsen JT, 2006, BOT REV, V72, P1, DOI 10.1663/0006-8101(2006)72[1:DADOFS]2.0.CO
[8]  
2
[9]   Herbivore-induced plant volatiles induce an indirect defence in neighbouring plants [J].
Kost, C ;
Heil, M .
JOURNAL OF ECOLOGY, 2006, 94 (03) :619-628
[10]  
Lee PH, 2005, B KOREAN CHEM SOC, V26, P157