A novel strategy for the enantioselective synthesis of the steroidal framework using cascade ring expansion reactions of small ring systems - Asymmetric total synthesis of (+)-equilenin

被引:37
作者
Nemoto, H [1 ]
Yoshida, M [1 ]
Fukumoto, K [1 ]
Ihara, M [1 ]
机构
[1] Tohoku Univ, Inst Pharmaceut, Sendai, Miyagi 9808578, Japan
关键词
asymmetric synthesis; rearrangement; steroids and sterols; stereocontrol;
D O I
10.1016/S0040-4039(98)02479-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantioselective synthesis of (+)-equilenin (1) utilizing a novel strategy is described. The key steps are two cascade ring expansion reactions of small ring systems; 1) chiral (salen)Mn-III complex-catalyzed cascade reaction of cyclopropylidene; 2) Pd-II-mediated cascade reaction of the cyclobutanol. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:907 / 910
页数:4
相关论文
共 18 条
[1]  
AKHREM AA, 1970, TOTAL STEROID SYNTHE
[2]  
ApSimon J., 1973, TOTAL SYNTHESIS NATU, V2
[3]   RESEARCH ON NITRO-DERIVATIVES OF BIOLOGICAL INTEREST .44. SYNTHESIS OF 2-NITRO-NAPHTHO[1,2-B]FURANS MONOMETHOXYLATED ON THE EXTERNAL HOMOCYCLE [J].
BILGER, C ;
DEMERSEMAN, P ;
ROYER, R .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1987, 22 (04) :363-365
[4]  
BIRCH AJ, 1967, TETRAHEDRON LETT, V23, P2763
[5]   REACTIONS OF CARBONYL-COMPOUNDS WITH GRIGNARD-REAGENTS IN THE PRESENCE OF CERIUM CHLORIDE [J].
IMAMOTO, T ;
TAKIYAMA, N ;
NAKAMURA, K ;
HATAJIMA, T ;
KAMIYA, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4392-4398
[6]   HIGHLY ENANTIOSELECTIVE EPOXIDATION CATALYSTS DERIVED FROM 1,2-DIAMINOCYCLOHEXANE [J].
JACOBSEN, EN ;
ZHANG, W ;
MUCI, AR ;
ECKER, JR ;
DENG, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) :7063-7064
[7]  
JOHNS WF, 1973, STEROIDS, V8
[8]   BIOMIMETIC POLYENE CYCLIZATIONS [J].
JOHNSON, WS .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (01) :9-17
[9]   ANNELATION REACTION BY USING HETEROCYCLIC-COMPOUNDS [J].
KAMETANI, T ;
NEMOTO, H .
HETEROCYCLES, 1978, 10 :349-390
[10]   RECENT ADVANCES IN THE TOTAL SYNTHESIS OF STEROIDS VIA INTRAMOLECULAR CYCLOADDITION REACTIONS [J].
KAMETANI, T ;
NEMOTO, H .
TETRAHEDRON, 1981, 37 (01) :3-16