PRACTICAL ENANTIOSELECTIVE SYNTHESIS OF THE CIGARETTE BEETLE SEX-PHEROMONE SERRICORNIN

被引:19
作者
CHAN, PCM [1 ]
CHONG, JM [1 ]
KOUSHA, K [1 ]
机构
[1] UNIV WATERLOO,GUELPH WATERLOO CTR GRAD WORK CHEM,DEPT CHEM,WATERLOO N2L 3G1,ON,CANADA
关键词
D O I
10.1016/S0040-4020(01)86986-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(4RS,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone (serricornin and its C4-epimer) may be prepared from oxazolidinone 5 in 8 steps with or overall yield of 33%.
引用
收藏
页码:2703 / 2714
页数:12
相关论文
共 34 条
[1]   AN IMPROVED, CONVENIENT PROCEDURE FOR REDUCTION OF AMINO-ACIDS TO AMINOALCOHOLS - USE OF NABH4-H2SO4 [J].
ABIKO, A ;
MASAMUNE, S .
TETRAHEDRON LETTERS, 1992, 33 (38) :5517-5518
[2]   SYNTHESIS OF 4RS,6S,7S-SERRICORNINE AND THE CORRESPONDING PAIR OF RACEMATES [J].
BAKER, R ;
DEVLIN, JA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (03) :147-148
[3]   INTRAMOLECULAR CLAISEN-TYPE CONDENSATIONS OF BETA-ACETOXY AMIDES OR IMIDES [J].
BRANDANGE, S ;
LEIJONMARCK, H .
TETRAHEDRON LETTERS, 1992, 33 (21) :3025-3028
[4]   A CONVENIENT PREPARATION OF (+/-)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID (MOSHER ACID) [J].
CHONG, JM ;
LOEWITH, R .
SYNTHETIC COMMUNICATIONS, 1993, 23 (15) :2145-2150
[5]  
CHUMAN T, 1979, TETRAHEDRON LETT, P2361
[6]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[7]   A CONVENIENT SYNTHESIS OF (2S)-2-AMINO-3-PHENYLPROPANOL [J].
DHARANIPRAGADA, R ;
ALARCON, A ;
HRUBY, VJ .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1991, 23 (03) :396-397
[8]   STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].
EVANS, DA ;
NELSON, JV ;
VOGEL, E ;
TABER, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3099-3111
[9]   ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].
EVANS, DA ;
BARTROLI, J ;
SHIH, TL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129
[10]   CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE [J].
EVANS, DA ;
BRITTON, TC ;
ELLMAN, JA .
TETRAHEDRON LETTERS, 1987, 28 (49) :6141-6144