Attempted stereocontrol at C-2′ of strigol-type compounds by a Michael reaction/elimination approach

被引:14
作者
Röhrig, S
Hennig, L
Findeisen, M
Welzel, P
Frischmuth, K
Marx, A
Petrowitsch, T
Koll, P
Müller, D
Mayer-Figge, H
Sheldrick, WS
机构
[1] Univ Leipzig, Fak Chem & Mineral, D-04103 Leipzig, Germany
[2] Ruhr Univ Bochum, Fak Chem, D-44780 Bochum, Germany
关键词
D O I
10.1016/S0040-4020(98)00076-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
By a Michael addition/nucleophilic substitution/elimination sequence the stereocontrol at C-2' in strigol-typed compounds is in principle possible. However, the method is unsuitable for practical application since it has been shown that a stereolabile intermediate is involved. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3413 / 3438
页数:26
相关论文
共 27 条
[21]  
Schmidt R. R., 1986, ANGEW CHEM, V98, P213
[22]   NEW METHODS FOR THE SYNTHESIS OF GLYCOSIDES AND OLIGOSACCHARIDES - ARE THERE ALTERNATIVES TO THE KOENIGS-KNORR METHOD [J].
SCHMIDT, RR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (03) :212-235
[23]   ANOMERIC-OXYGEN ACTIVATION FOR GLYCOSIDE SYNTHESIS - THE TRICHLOROACETIMIDATE METHOD [J].
SCHMIDT, RR ;
KINZY, W .
ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, VOL 50, 1994, 50 :21-123
[24]   ENANTIOMERICALLY PURE CYCLOALKENYLACETIC-ACID DERIVATIVES VIA PD-CATALYZED ASYMMETRIC ALLYLIC ALKYLATION AND SUBSEQUENT ENANTIOMERIC ENRICHMENT VIA IODOLACTONES [J].
SENNHENN, P ;
GABLER, B ;
HELMCHEN, G .
TETRAHEDRON LETTERS, 1994, 35 (46) :8595-8598
[25]   RECENT PROGRESS IN O-GLYCOSYLATION METHODS AND ITS APPLICATION TO NATURAL-PRODUCTS SYNTHESIS [J].
TOSHIMA, K ;
TATSUTA, K .
CHEMICAL REVIEWS, 1993, 93 (04) :1503-1531
[26]   ASYMMETRIC INDUCTION IN ALLYLIC ALKYLATIONS OF 3-(ACYLOXY)CYCLOALKENES [J].
TROST, BM ;
BUNT, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (09) :4089-4090
[27]  
TROST BM, 1978, CHEM REV, V78, P362