SYNTHESIS OF EARTHY-MOLDY SMELLING COMPOUNDS .2. ETHYL ALPHA-FENCHOLS AND BETA-FENCHOLS

被引:9
作者
GOSSELIN, P [1 ]
JOULAIN, D [1 ]
LAURIN, P [1 ]
ROUESSAC, F [1 ]
机构
[1] ROBERTET SA, F-06333 GRASSE, FRANCE
关键词
D O I
10.1016/S0040-4039(00)94718-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several stereoselective routes to both ethyl α- and β- fenchols 1α and 1β are discussed. Direct addition of ethyllithium to fenchone was the best route to 1α whereas obtention of 1β was achieved through the highly stereoselective retroethynylation of a mixture of ethynyl α- and β-fenchols 4α and 4β. © 1990.
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页码:3151 / 3154
页数:4
相关论文
共 16 条
[1]  
ANTKOWIAK WZ, 1966, B ACAD POL SCI-CHIM, V14, P437
[2]  
BESSIERE Y, 1972, B SOC CHIM FR, P1000
[3]  
CHODKIEWICZ W, 1968, CR ACAD SCI C CHIM, V267, P911
[4]  
CHODKIEWICZ W, 1968, B SOC CHIM FR, P3323
[5]   DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS [J].
COREY, EJ ;
CHAYKOVSKY, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1353-+
[6]   ALPHA-LITHIOMETHYLENETRIPHENYLPHOSPHORANE, A HIGHLY REACTIVE YLIDE EQUIVALENT [J].
COREY, EJ ;
KANG, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (17) :4724-4725
[7]   SULTONE REARRANGEMENTS .1. 10-ISOBORNYL AND 4-METHYL-10-ISOBORNYL SULTONES [J].
DIMMEL, DR ;
FU, WY .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (21) :3778-3782
[8]   THE WITTIG REACTION USING POTASSIUM-TERT-BUTOXIDE HIGH-YIELD METHYLENATIONS OF STERICALLY HINDERED KETONES [J].
FITJER, L ;
QUABECK, U .
SYNTHETIC COMMUNICATIONS, 1985, 15 (10) :855-864
[9]   SYNTHESIS OF EARTHY-MOLDY SMELLING COMPOUNDS .1. STEREOSELECTIVE SYNTHESIS OF (+/-)-GEOSMIN [J].
GOSSELIN, P ;
JOULAIN, D ;
LAURIN, P ;
ROUESSAC, F .
TETRAHEDRON LETTERS, 1989, 30 (21) :2775-2778
[10]   CERIUM CHLORIDE-PROMOTED NUCLEOPHILIC-ADDITION OF GRIGNARD-REAGENTS TO KETONES AN EFFICIENT METHOD FOR THE SYNTHESIS OF TERTIARY ALCOHOLS [J].
IMAMOTO, T ;
TAKIYAMA, N ;
NAKAMURA, K .
TETRAHEDRON LETTERS, 1985, 26 (39) :4763-4766