INTRAMOLECULAR [3+2]CYCLOADDITIONS - SYNTHESIS OF 1-METHYLENE-2,3,3A,4,5,9B-HEXAHYDRO-1H-BENZ[E]INDENES AND AN UNSUCCESSFUL APPROACH TO ERGOT ALKALOIDS

被引：10

作者：

COLLINS, MP ^{[1
]}

DREW, MGB ^{[1
]}

MANN, J ^{[1
]}

FINCH, H ^{[1
]}

机构：

[1] GLAXO GRP RES LTD,WARE SG12 0DJ,HERTS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 23期

关键词：

D O I：

10.1039/p19920003211

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-(1-Hydroxy-2-trimethylsilylmethylprop-2-enyl)-2-(4-substituted-but-3-enyl)-4-methoxybenzenes, prepared by a short synthesis, underwent intramolecular [3 + 2]cycloadditions to produce the title indenes. An analogous intramolecular cycloaddition was attempted with N-benzyl-4-(2-methoxyvinyl)-3-(2-hydroxy-3-trimethylsilylmethylbut-3-enyl)indoline, in an attempt to produce a key intermediate for ergot alkaloid synthesis, but this was unsuccessful.

引用

页码：3211 / 3217

页数：7

共 17 条

[1] BARBOSA LCD, 1992, J CHEM SOC PERK T 1, P337
[2] EFFECTIVE, THERMAL 3-CARBON + 2-CARBON CYCLOADDITION FOR CYCLOPENTENONE FORMATION - FORMAL 1,3-DIPOLAR CYCLOADDITION OF CYCLOPROPENONE KETALS
BOGER, DL
BROTHERTON, CE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (03) : 805 - 807
[3] INTRAMOLECULAR (3 + 2) CYCLOADDITIONS
COLLINS, MP
MANN, J
CAPPS, N
FINCH, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01): : 239 - 240
[4] (TRIMETHYLSILYL)CYCLOPENTENE ANNULATION - A REGIOCONTROLLED APPROACH TO THE SYNTHESIS OF 5-MEMBERED RINGS
DANHEISER, RL
CARINI, DJ
BASAK, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (06) : 1604 - 1606
[5] GIGUERE RJ, 1990, TETRAHEDRON LETT, P4577
[6] GIGUERE RJ, 1988, TETRAHEDRON LETT, P6071
[7] SYNTHESES OF 7-MEMBERED AND 5-MEMBERED RINGS FROM ALLYL CATIONS
HOFFMANN, HM
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1973, 12 (10) : 819 - 835
[8] NUCLEOPHILIC ORGANO-SILICON INTERMEDIATES TURNED ELECTROPHILIC - (TRIMETHYLSILYL)METHYL, TRIMETHYLSILYLOXY AND ALSO 2-TETRAHYDROPYRANYLOXY AS TERMINATORS OF CYCLO-ADDITIONS OF ALLYL CATIONS - A SHORT ROUTE TO DEHYDROZIZAENES (6-METHYLENETRICYCLO[6.2.1.01,5]-UNDEC-9,10-ENES) AND RELATED TRICYCLES AND [3.2.1]-BICYCLESI
HOFFMANN, HMR
EGGERT, U
GIBBELS, U
GIESEL, K
KOCH, O
LIES, R
RABE, J
[J]. TETRAHEDRON, 1988, 44 (13) : 3899 - 3918
[9] THE CYCLOADDITION OF ALLYL CATIONS TO 1,3-DIENES - GENERAL-METHOD FOR THE SYNTHESIS OF 7-MEMBERED CARBOCYCLES
HOFFMANN, HMR
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (01): : 1 - 19
[10] INTRAMOLECULAR ADDITION OF 2-(TRIMETHYLSILYL)METHYL-SUBSTITUTED ALKYL CATIONS TO DOUBLE-BONDS - SYNTHESIS OF BICYCLO[3.3.0]OCTANE DERIVATIVES
IPAKTSCHI, J
LAUTERBACH, G
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (04): : 354 - 356

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