FACILE SYNTHESIS OF (-)-SERRICORNIN BY MEANS OF PALLADIUM-CATALYZED HYDROGENOLYSIS OF ALKENYLOXIRANES

被引:39
作者
SHIMIZU, I
HAYASHI, K
IDE, N
OSHIMA, M
机构
[1] Department of Applied Chemistry, School of Science and Engineering, Waseda University, Shinjuku-ku, Tokyo
关键词
D O I
10.1016/S0040-4020(01)96030-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral synthesis of (-)-serricornin by using palladium-catalyzed stereoselective hydrogenolysis of the alkenyloxirane to the homoallylic alcohol with formic acid as a key step was carried out.
引用
收藏
页码:2991 / 2998
页数:8
相关论文
共 20 条
[1]  
CHUMAN T, 1979, TETRAHEDRON LETT, P2361
[2]  
COFFELT JA, 1972, ANN ENTOMOL SOC AM, P477
[3]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[4]   PROCEDURE FOR THE CATALYTIC ASYMMETRIC EPOXIDATION OF ALLYLIC ALCOHOLS IN THE PRESENCE OF MOLECULAR-SIEVES [J].
HANSON, RM ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) :1922-1925
[5]   SYNTHESES OF OPTICALLY-ACTIVE INSECT PHEROMONES, (2R,5S)-2-METHYL-5-HEXANOLIDE, (3S,11S)-3,11-DIMETHYL-2-NONACOSANONE, AND SERRICORNIN [J].
KATSUKI, T ;
YAMAGUCHI, M .
TETRAHEDRON LETTERS, 1987, 28 (06) :651-654
[6]   THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].
KATSUKI, T ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976
[7]   DIASTEREOSELECTIVE AND ENANTIOSELECTIVE PREPARATION OF BETA-ALKYLHOMOALLYLIC ALCOHOLS - SYNTHESIS OF SERRICORNIN AND CORYNOMYCOLIC ACID [J].
KOBAYASHI, Y ;
KITANO, Y ;
TAKEDA, Y ;
SATO, F .
TETRAHEDRON, 1986, 42 (11) :2937-2943
[8]   PYRAZOLINES .V. RING CLOSURE TO OXYGEN IN PYROLYSIS OF 3-ACETYL-DELTA1-PYRAZOLINES [J].
MCGREER, DE ;
CHIU, NWK ;
VINJE, MG .
CANADIAN JOURNAL OF CHEMISTRY, 1965, 43 (05) :1398-&
[9]   PHERMONE SYNTHESIS .53. SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF SERRICORNIN [(4S, 6S, 7S)-4,6-DIMETHYL-7-HYDROXY-3-NONANONE] - THE SEX-PHEROMONE OF THE CIGARETTE BEETLE [J].
MORI, K ;
NOMI, H ;
CHUMAN, T ;
KOHNO, M ;
KATO, K ;
NOGUCHI, M .
TETRAHEDRON, 1982, 38 (24) :3705-3711
[10]   PHEROMONE SYNTHESIS .66. A NEW SYNTHESIS OF SERRICORNIN [(4S,6S,7S)-7-HYDROXY-4,6-DIMETHYL-3-NONANONE], THE SEX-PHEROMONE OF THE CIGARETTE BEETLE [J].
MORI, K ;
WATANABE, H .
TETRAHEDRON, 1985, 41 (16) :3423-3428