e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis of prenylated indoles

E Wenkert, EC Angell, VF Ferreira…

Index: Wenkert, Ernest; Angell, E. Charles; Ferreira, Vitor F.; Michelotti, Enrique L.; Piettre, Serge R.; et al. Journal of Organic Chemistry, 1986 , vol. 51, # 12 p. 2343 - 2351

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Citation Number: 74

Abstract

Interaction of magnesium indolates and allyl oxides in the presence of bis (tripheny1phosphine) nickel dichloride results in indole P-allylation, except in cases involving highly substituted indoles and allyl alcohols. This method permits the@- prenylation of indole and a-prenylation of ketones (by way of their magnesium enaminates). Base-induced interaction of ethynyldimethylcarbinyl chloride and indole under a variety of ...

2-Methyl-3-buten-2-ol Structure

2-Methyl-3-bute...

N-cyclohexylcyclopentanimine Structure

N-cyclohexylcyc...

~%

penten-1-yl cyclopentanone Structure

penten-1-yl cyc...

2-(2-methylbut-3-en-2-yl)cyclopentan-1-one Structure

2-(2-methylbut-...

chlorophenylsulfone Structure

chlorophenylsulfone

~%

1-[1-(benzenesulfonyl)indol-2-yl]-3-methylbut-2-en-1-one Structure

1-[1-(benzenesu...

3-Bromoindole Structure

~%

1-[1-(benzenesulfonyl)indol-2-yl]-3-methylbut-2-en-1-one Structure

1-[1-(benzenesu...

3-Bromo-1-(phenylsulfonyl)indole Structure

3-Bromo-1-(phen...

~%

1-[1-(benzenesulfonyl)indol-2-yl]-3-methylbut-2-en-1-one Structure

1-[1-(benzenesu...

3-methylcrotonoyl chloride Structure

3-methylcrotono...

1-(Phenylsulfonyl)-1H-indole Structure

1-(Phenylsulfon...

~%

1-[1-(benzenesulfonyl)indol-2-yl]-3-methylbut-2-en-1-one Structure

1-[1-(benzenesu...

3-methylcrotonoyl chloride Structure

3-methylcrotono...

3-Bromo-1-(phenylsulfonyl)indole Structure

3-Bromo-1-(phen...

~%

1-[1-(benzenesulfonyl)indol-3-yl]-3-methylbut-2-en-1-one Structure

1-[1-(benzenesu...

1-[1-(benzenesulfonyl)indol-2-yl]-3-methylbut-2-en-1-one Structure

1-[1-(benzenesu...

3-Bromoindole Structure

~%

1-(Phenylsulfonyl)-1H-indole Structure

1-(Phenylsulfon...

chlorophenylsulfone Structure

chlorophenylsulfone

~%

1-(Phenylsulfonyl)-1H-indole Structure

1-(Phenylsulfon...

3-Bromo-1-(phenylsulfonyl)indole Structure

3-Bromo-1-(phen...

3,3-Dimethylallyl bromide Structure

3,3-Dimethylall...

~%

1-(Phenylsulfonyl)-1H-indole Structure

1-(Phenylsulfon...

1-(benzenesulfonyl)-3-(3-methylbut-2-enyl)indole Structure

1-(benzenesulfo...

1-(allyl)-1H-indole Structure

1-(allyl)-1H-indole

~%

3-(2-PROPENYL)INDOLE Structure

3-(2-PROPENYL)INDOLE

1-(benzenesulfonyl)-3-(3-methylbut-2-enyl)indole Structure

1-(benzenesulfo...

~94%

3-(dimethylallyl)indole Structure

3-(dimethylally...

β-D-Lac-SH Structure

~8%

3-(dimethylallyl)indole Structure

3-(dimethylally...

1-(1H-indol-3-yl)-3-methylbutan-1-one Structure

1-(1H-indol-3-y...

1-(allyl)-1H-indole Structure

1-(allyl)-1H-indole

~%

3-(dimethylallyl)indole Structure

3-(dimethylally...

Indole Structure

~%

3-(dimethylallyl)indole Structure

3-(dimethylally...

3-Bromoindole Structure

~%

3-(dimethylallyl)indole Structure

3-(dimethylally...

3-Bromo-1-(phenylsulfonyl)indole Structure

3-Bromo-1-(phen...

~%

3-(dimethylallyl)indole Structure

3-(dimethylally...

1-[1-(benzenesulfonyl)indol-3-yl]-3-methylbut-2-en-1-one Structure

1-[1-(benzenesu...

~%

3-(dimethylallyl)indole Structure

3-(dimethylally...

Indole Structure

3,3-Dimethylallyl bromide Structure

3,3-Dimethylall...

~%

3-(dimethylallyl)indole Structure

3-(dimethylally...

N/A Structure

3-Bromoindole Structure

~%

1-(benzenesulfonyl)-3-(3-methylbut-2-enyl)indole Structure

1-(benzenesulfo...

chlorophenylsulfone Structure

chlorophenylsulfone

~%

1-(benzenesulfonyl)-3-(3-methylbut-2-enyl)indole Structure

1-(benzenesulfo...

3-Bromo-1-(phenylsulfonyl)indole Structure

3-Bromo-1-(phen...

3,3-Dimethylallyl bromide Structure

3,3-Dimethylall...

~%

1-(Phenylsulfonyl)-1H-indole Structure

1-(Phenylsulfon...

1-(benzenesulfonyl)-3-(3-methylbut-2-enyl)indole Structure

1-(benzenesulfo...

3-Bromoindole Structure

~%

lithium,1-(benzenesulfonyl)-2H-indol-2-ide Structure

lithium,1-(benz...

3-Bromo-1-(phenylsulfonyl)indole Structure

3-Bromo-1-(phen...

~%

lithium,1-(benzenesulfonyl)-2H-indol-2-ide Structure

lithium,1-(benz...

chlorophenylsulfone Structure

chlorophenylsulfone

~%

lithium,1-(benzenesulfonyl)-2H-indol-2-ide Structure

lithium,1-(benz...

Indole Structure

~%

1-[1-(benzenesulfonyl)indol-3-yl]-3-methylbut-2-en-1-one Structure

1-[1-(benzenesu...

1-(allyl)-1H-indole Structure

1-(allyl)-1H-indole

~%

1-[1-(benzenesulfonyl)indol-3-yl]-3-methylbut-2-en-1-one Structure

1-[1-(benzenesu...

3-Bromoindole Structure

~%

1-[1-(benzenesulfonyl)indol-3-yl]-3-methylbut-2-en-1-one Structure

1-[1-(benzenesu...

chlorophenylsulfone Structure

chlorophenylsulfone

~%

1-[1-(benzenesulfonyl)indol-3-yl]-3-methylbut-2-en-1-one Structure

1-[1-(benzenesu...

β-D-Lac-SH Structure

chlorophenylsulfone Structure

chlorophenylsulfone

~%

1-[1-(benzenesulfonyl)indol-3-yl]-3-methylbut-2-en-1-one Structure

1-[1-(benzenesu...

3-methylcrotonoyl chloride Structure

3-methylcrotono...

3-Bromo-1-(phenylsulfonyl)indole Structure

3-Bromo-1-(phen...

~%

1-[1-(benzenesulfonyl)indol-3-yl]-3-methylbut-2-en-1-one Structure

1-[1-(benzenesu...

1-[1-(benzenesulfonyl)indol-2-yl]-3-methylbut-2-en-1-one Structure

1-[1-(benzenesu...

Lewis Acid Alkylation of Ketones Using SN1-reactive Acetates

[Reetz, M. T.; Huettenhain, S.; Huebner, F. Synthetic Communications, 1981 , vol. 11, # 3 p. 217 - 222]

Convenient Radical. ALPHA.-Monoallylations of Carbonyl Compo...

[Watanabe, Yoshihiko; Yoneda, Tetsuo; Okumura, Tatsuya; Ueno, Yoshio; Toru, Takeshi Bulletin of the Chemical Society of Japan, 1993 , vol. 66, # 10 p. 3030 - 3033]