DIASTEREOSELECTIVE ALKYLATION OF CHIRAL TIN(II) ENOLATES ONTO CYCLIC ACYL IMINIUM IONS - ASYMMETRIC TOTAL SYNTHESIS OF (-)-SUPINIDINE

被引:32
作者
NAGAO, Y [1 ]
DAI, WM [1 ]
OCHIAI, M [1 ]
SHIRO, M [1 ]
机构
[1] SHIONOGI & CO LTD,SHIONOGI RES LAB,FUKUSHIMA KU,OSAKA 553,JAPAN
关键词
D O I
10.1016/S0040-4020(01)96008-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The scope and mechanism of the asymmetric alkylation of chiral tin (II) enolate 10 with cyclic acyl iminium ion 5 were investigated. An application of the reaction to the asymmetric synthesis of (-)-supinidine was also achieved. © 1990.
引用
收藏
页码:6361 / 6380
页数:20
相关论文
共 28 条
[11]   NABH4 REDUCTION OF CYCLIC IMIDES [J].
HUBERT, JC ;
WIJNBERG, JBP ;
SPECKAMP, WN .
TETRAHEDRON, 1975, 31 (11-1) :1437-1441
[12]  
IWASAWAN, 1986, J SYN ORG CHEM JPN, P71
[13]   AMIDOALKYLATION IN ORGANIC-SYNTHESIS .1. TOTAL SYNTHESIS OF ISORETRONECANOL AND TRACHELANTHAMIDINE [J].
KRAUS, GA ;
NEUENSCHWANDER, K .
TETRAHEDRON LETTERS, 1980, 21 (40) :3841-3844
[14]   NEW CHIRAL RECOGNITION OF CHIRAL TIN(II) ENOLATES TOWARD CYCLIC ACYL IMINIUM SPECIES - ASYMMETRIC TOTAL SYNTHESIS OF (-)-SUPINIDINE [J].
NAGAO, Y ;
DAI, WM ;
OCHIAI, M .
TETRAHEDRON LETTERS, 1988, 29 (47) :6133-6136
[15]   HIGHLY DIASTEREOSELECTIVE ALKYLATION ONTO 4-ACETOXY-2-AZETIDINONES EMPLOYING TIN(II) ENOLATES OF C4-CHIRAL 3-ACYL-1,3-THIAZOLIDINE-2-THIONES [J].
NAGAO, Y ;
KUMAGAI, T ;
TAMAI, S ;
ABE, T ;
KURAMOTO, Y ;
TAGA, T ;
AOYAGI, S ;
NAGASE, Y ;
OCHIAI, M ;
INOUE, Y ;
FUJITA, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4673-4675
[16]   ASYMMETRIC TOTAL SYNTHESIS OF A NEW NON-NATURAL 1-BETA-METHOXYCARBAPENEM [J].
NAGAO, Y ;
ABE, T ;
SHIMIZU, H ;
KUMAGAI, T ;
INOUE, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (13) :821-823
[17]   EXTREMELY SHORT CHIRAL SYNTHESIS OF BICYCLIC ALKALOIDS HAVING A NITROGEN ATOM RING JUNCTURE [J].
NAGAO, Y ;
DAI, WM ;
OCHIAI, M ;
TSUKAGOSHI, S ;
FUJITA, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (01) :289-291
[18]   NEW C4-CHIRAL 1,3-THIAZOLIDINE-2-THIONES - EXCELLENT CHIRAL AUXILIARIES FOR HIGHLY DIASTEREOCONTROLLED ALDOL-TYPE REACTIONS OF ACETIC-ACID AND ALPHA,BETA-UNSATURATED ALDEHYDES [J].
NAGAO, Y ;
HAGIWARA, Y ;
KUMAGAI, T ;
OCHIAI, M ;
INOUE, T ;
HASHIMOTO, K ;
FUJITA, E .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (12) :2391-2393
[19]  
NAGAO Y, IN PRESS J ORG CHEM
[20]  
NAGAO Y, 1986, J CHEM SOC CHEM COMM, P602