An efficient asymmetric synthesis of allo- and pseudo-7,8-dimethoxyberbane systems through tin-mediated three component coupling

被引：18

作者：

Haraguchi, Y ^{[1
]}

Kozima, S ^{[1
]}

Yamaguchi, R ^{[1
]}

机构：

[1] KYOTO UNIV,FAC INTEGRATED HUMAN STUDIES,DEPT NAT & ENVIRONM SCI,YOSHIDA,KYOTO 606,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 02期

关键词：

D O I：

10.1016/0957-4166(96)00027-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Three component coupling reactions of chiral 3-substituted 6,7-dimethoxy-3,4-dihydroisoquinoline with allylic tin reagents and unsaturated acid chlorides followed by intramolecular Diels-Alder reactions afford allo- and pseudo-7,8-dimethoxyberbane systems in high diastereomeric excess.

引用

页码：443 / 449

页数：7

共 12 条

[1]

BHAKUNI DS, 1986, ALKALOIDS, V28, P95

[2]

DORNYEI G, 1994, HETEROCYCLES, V39, P449

[3] HIGH 1,3-ASYMMETRIC INDUCTION IN ADDITION OF ALLYLIC TIN REAGENTS TO CHIRAL 3-SUBSTITUTED 3,4-DIHYDROISOQUINOLINES ACTIVATED BY ACYL CHLORIDES [J].

HATANO, B ;

HARAGUCHI, Y ;

KOZIMA, S ;

YAMAGUCHI, R .

CHEMISTRY LETTERS, 1995, (11) :1003-1004

[4]

OREILLY NJ, 1990, SYNTHESIS-STUTTGART, P550

[5] THE ABSOLUTE CONFIGURATION OF LIGNANS [J].

SCHRECKER, AW ;

HARTWELL, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (14) :3827-3831

[6] BERBANES - A NEW CLASS OF SELECTIVE ALPHA-2-ADRENOCEPTOR ANTAGONISTS [J].

VIZI, ES ;

TOTH, I ;

SOMOGYI, GT ;

SZABO, L ;

HARSING, LG ;

SZANTAY, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (08) :1355-1359

[7] A HIGHLY EFFECTIVE ONE-POT BICYCLOANNULATION METHODOLOGY FOR THE SYNTHESIS OF BERBAN AND YOHIMBAN SYSTEMS BASED ON ORGANOTIN-MEDIATED 3-COMPONENT COUPLING (N-ACYLATIVE PENTADIENYLATION OF C=N BONDS) [J].

YAMAGUCHI, R ;

HAMASAKI, T ;

SASAKI, T ;

OHTA, T ;

UTIMOTO, K ;

KOZIMA, S ;

TAKAYA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1136-1143

[8] SIMULTANEOUS 1,2-INTRODUCTION OF ALLYLIC AND ALPHA-BETA-GAMMA-DELTA-UNSATURATED ACYL-GROUPS INTO ISOQUINOLINE SYSTEMS AND SUBSEQUENT INTRAMOLECULAR DIELS-ALDER REACTIONS [J].

YAMAGUCHI, R ;

OTSUJI, A ;

UTIMOTO, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2186-2187

[9] REACTION OF ALLYLIC TIN REAGENTS WITH NITROGEN HETEROAROMATICS ACTIVATED BY ALKYL CHLOROFORMATES - REGIOSELECTIVE SYNTHESIS OF ALPHA-ALLYLATED 1,2-DIHYDROPYRIDINES AND CHANGE OF THE REGIOSELECTIVITY DEPENDING ON METHYL SUBSTITUENTS AT THE ALLYLIC MOIETY [J].

YAMAGUCHI, R ;

MORIYASU, M ;

YOSHIOKA, M ;

KAWANISI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3507-3512

[10] DIVERGENT CHANGE OF REGIOSELECTIVITY IN NUCLEOPHILIC-ADDITION OF ELECTRON-DEFICIENT ALLYLIC TIN REAGENTS TO 4-ACYLPYRIDINIUM SALTS - SELECTIVE FORMATION OF 4,4-DISUBSTITUTED 1,4-DIHYDROPYRIDINES [J].

YAMAGUCHI, R ;

MOCHIZUKI, K ;

KOZIMA, S ;

TAKAYA, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (12) :981-982

← 1 2 →