VITAMIN-B12-CATALYZED C,C-BOND FORMATION - SYNTHESIS OF A CALIFORNIA RED SCALE PHEROMONE

被引:17
作者
AUER, L
WEYMUTH, C
SCHEFFOLD, R
机构
[1] Institut Für Organische Chemie, Universität Bern, Bern, CH-3012
关键词
D O I
10.1002/hlca.19930760205
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A mixture of (3S,6R)-and(3R,6R)-3-methyl-6-(1-methylethenyl)dec-9)-enyl acetate (1a and 1b, respectively) - 1a being a pheromone of the California red scale - is synthesized in 14 steps from (+)-(R)-limonene (4). The key step is the reductive vitamin-B-12-catalyzed coupling of(R)-5-(2-iodoethyl)-6-methylhept-6-en-2-one ethylene acetal (8) and methyl crotonate (3).
引用
收藏
页码:810 / 818
页数:9
相关论文
共 19 条
[1]   SYNTHESIS OF THE OPTICAL ISOMERS OF "3-METHYL-6-ISOPROPENYL-9-DECEN-1-YL ACETATE, A COMPONENT OF THE CALIFORNIA RED SCALE PHEROMONE [J].
ANDERSON, RJ ;
ADAMS, KG ;
CHINN, HR ;
HENRICK, CA .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (11) :2229-2236
[2]   DIASTEREOSELECTIVE SYNTHESIS OF (3S,6R)-6-ISOPROPENYL-3-METHYL-9-DECENYL ACETATE, A CONSTITUENT OF CALIFORNIA RED SCALE (AONIDIELLA-AURANTII) SEX-PHEROMONE [J].
BAUDOUY, R ;
MALIVERNEY, C .
TETRAHEDRON, 1988, 44 (02) :471-480
[3]   NEW SYNTHESIS OF THE CALIFORNIA RED SCALE SEX-PHEROMONE [J].
BECKER, D ;
SAHALI, Y .
TETRAHEDRON, 1988, 44 (14) :4541-4546
[4]  
BOSE AK, 1973, TETRAHEDRON LETT, P3937
[5]  
BUSATO S, 1990, TETRAHEDRON, V46, P3165
[6]   ATOM TRANSFER CYCLIZATION REACTIONS OF ALPHA-IODO ESTERS, KETONES, AND MALONATES - EXAMPLES OF SELECTIVE 5-EXO, 6-ENDO, 6-EXO, AND 7-ENDO RING CLOSURES [J].
CURRAN, DP ;
CHANG, CT .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3140-3157
[7]   SYNTHESIS OF THE AI COMPONENT OF THE RED SAN-JOSE SCALE SEX-PHEROMONE [J].
DRAGAN, VA ;
VESELOVSKII, VV ;
MOISEENKOV, AM .
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1989, 38 (05) :1038-1041
[8]   THIOUREA, A CONVENIENT REAGENT FOR THE REDUCTIVE CLEAVAGE OF OLEF IN OZONOLYSIS PRODUCTS [J].
GUPTA, D ;
SOMAN, R ;
DEV, S .
TETRAHEDRON, 1982, 38 (20) :3013-3018
[9]   DEHYDROHALOGENATION REACTIONS USING HINDERED LITHIUM DIALKYLAMIDE BASES [J].
KOPKA, IE ;
NOWAK, MA ;
RATHKE, MW .
SYNTHETIC COMMUNICATIONS, 1986, 16 (01) :27-34
[10]  
LIPTON MF, 1980, J ORGANOMET CHEM, V186, P155