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

来源：

TETRAHEDRON | 1990年 / 46卷 / 18期

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

页码：6361 / 6380

页数：20

共 28 条

[1] TRIFLUOROMETHYL SULFATES OF TIN [J].

BATCHELOR, RJ ;

RUDDICK, JNR ;

SAMS, JR ;

AUBKE, F .

INORGANIC CHEMISTRY, 1977, 16 (06) :1414-1417

[2] SYNTHESIS OF ENDO-1-ETHOXYCARBONYL-PYRROLIZIDINE AND EXO-1-ETHOXYCARBONYLPYROLIZIDINE [J].

BRANDANGE, S ;

LUNDIN, C .

ACTA CHEMICA SCANDINAVICA, 1971, 25 (07) :2447-+

[3] PYRROLIZIDINONE AND INDOLIZIDINONE SYNTHESIS - GENERATION AND INTRAMOLECULAR ADDITION OF ALPHA-ACYLAMINO RADICALS TO OLEFINS AND ALLENES [J].

BURNETT, DA ;

CHOI, JK ;

HART, DJ ;

TSAI, YM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (26) :8201-8209

[4] CATIONIC CYCLIZATIONS OF KETENE DITHIOACETALS - A GENERAL-SYNTHESIS OF PYRROLIZIDINE, INDOLIZIDINE, AND QUINOLIZIDINE ALKALOID RING-SYSTEMS [J].

CHAMBERLIN, AR ;

NGUYEN, HD ;

CHUNG, JYL .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (10) :1682-1688

[5] ENANTIOSELECTIVE SYNTHESIS OF 7 PYRROLIZIDINE DIOLS FROM A SINGLE PRECURSOR [J].

CHAMBERLIN, AR ;

CHUNG, JYL .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) :4425-4431

[6] THE ALKALOIDS OF HELIOTROPIUM-EUROPAEUM L .2. ISOLATION AND STRUCTURES OF THE 3RD MAJOR ALKALOID AND 2 MINOR ALKALOIDS, AND ISOLATION OF THE PRINCIPAL N-OXIDES [J].

CULVENOR, CCJ .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1954, 7 (03) :287-297

[7] ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].

EVANS, DA ;

CHAPMAN, KT ;

BISAHA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256

[8] ALPHA-ACYLAMINO RADICAL CYCLIZATIONS - SYNTHESES OF ISORETRONECANOL [J].

HART, DJ ;

TSAI, YM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (26) :8209-8217

[9] A NUCLEAR MAGNETIC RESONANCE INVESTIGATION OF MOLECULAR COMPLEXES OF POLAR MOLECULES IN AROMATIC SOLVENTS [J].

HATTON, JV ;

SCHNEIDER, WG .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1962, 40 (07) :1285-&

[10]

Hiemstra H., 1988, ALKALOIDS, V32, P271

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