Syntheses and Diels-Alder cycloaddition reactions of 4H-furo [3, 4-b] indoles. A regiospecific Diels-Alder synthesis of ellipticine

…, MG Saulnier, B Pelcman, TC Barden…

Index: Gribble; Keavy; Davis; Saulnier; Pelcman; Barden; Sibi; Olson; BelBruno Journal of Organic Chemistry, 1992 , vol. 57, # 22 p. 5878 - 5891

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Citation Number: 100

Abstract

Seven examples of the novel 4H-furo [3, 4-b] indole ring system (3-9)-a stable, synthetic analogue of indole-2, 3-quinodimethane-have been synthesized in 6-8 steps from simple indoles in overall yields of 21-28%. These 4H-furo [3, 4-b] indoles undergo Diels-Alder reactions with several dienophiles (dimethyl acetylenedicarboxylate, N-phenylmaleimide, benzyne), including ethyl acrylate, which reacts regiospecifically with furoindole 4 to afford ...

 Related Synthetic Route
Indole-3-carboxaldehyde Structure

487-89-8

Indole-3-carbox...

~%

1-(benzenesulfonyl)-3-(hydroxymethyl)indole-2-carbaldehyde Structure

89241-34-9

1-(benzenesulfo...

1-(Phenylsulfonyl)-3-indolecarboxaldehyde Structure

80360-20-9

1-(Phenylsulfon...

~%

1-(benzenesulfonyl)-3-(hydroxymethyl)indole-2-carbaldehyde Structure

89241-34-9

1-(benzenesulfo...

chlorophenylsulfone Structure

98-09-9

chlorophenylsulfone

~%

1-(benzenesulfonyl)-3-(hydroxymethyl)indole-2-carbaldehyde Structure

89241-34-9

1-(benzenesulfo...

methyl formate Structure

107-31-3

methyl formate

[1-(PHENYLSULFONYL)-1H-INDOL-3-YL]METHANOL Structure

89241-33-8

[1-(PHENYLSULFO...

~%

1-(benzenesulfonyl)-3-(hydroxymethyl)indole-2-carbaldehyde Structure

89241-34-9

1-(benzenesulfo...

1-[3-methyl-1-(phenylsulfonyl)indol-2-yl]ethanol Structure

143774-62-3

1-[3-methyl-1-(...

~89%

1-[1-(benzenesulfonyl)-3-methylindol-2-yl]ethanone Structure

143774-63-4

1-[1-(benzenesu...

3-Methyl-1-(phenylsulfonyl)-1H-indole Structure

58550-84-8

3-Methyl-1-(phe...

~%

1-[1-(benzenesulfonyl)-3-methylindol-2-yl]ethanone Structure

143774-63-4

1-[1-(benzenesu...

3-Methylindole Structure

83-34-1

3-Methylindole

~%

1-[1-(benzenesulfonyl)-3-methylindol-2-yl]ethanone Structure

143774-63-4

1-[1-(benzenesu...

chlorophenylsulfone Structure

98-09-9

chlorophenylsulfone

~%

1-[1-(benzenesulfonyl)-3-methylindol-2-yl]ethanone Structure

143774-63-4

1-[1-(benzenesu...

1-(benzenesulfonyl)-3-(hydroxymethyl)indole-2-carbaldehyde Structure

89241-34-9

1-(benzenesulfo...

~46%

4-(benzenesulfonyl)furo[3,4-b]indole Structure

89241-37-2

4-(benzenesulfo...

[1-(PHENYLSULFONYL)-1H-INDOL-3-YL]METHANOL Structure

89241-33-8

[1-(PHENYLSULFO...

~%

4-(benzenesulfonyl)furo[3,4-b]indole Structure

89241-37-2

4-(benzenesulfo...

1-(Phenylsulfonyl)-3-indolecarboxaldehyde Structure

80360-20-9

1-(Phenylsulfon...

~99%

[1-(PHENYLSULFONYL)-1H-INDOL-3-YL]METHANOL Structure

89241-33-8

[1-(PHENYLSULFO...

Indole-3-carboxaldehyde Structure

487-89-8

Indole-3-carbox...

~%

[1-(PHENYLSULFONYL)-1H-INDOL-3-YL]METHANOL Structure

89241-33-8

[1-(PHENYLSULFO...

N/A Structure

143774-68-9

N/A

~49%

4-(benzenesulfonyl)-3-phenylfuro[3,4-b]indole Structure

143774-52-1

4-(benzenesulfo...

2-(p-methoxbenzyl)-1,2,3,4-tetrahydro-5,11-dimethylpyrido(4,3-b)carbazole Structure

128773-76-2

2-(p-methoxbenz...

~17%

ELLIPTICINE Structure

519-23-3

ELLIPTICINE

Formaldehyde Structure

50-00-0

Formaldehyde

1-(Phenylsulfonyl)-1H-indole Structure

40899-71-6

1-(Phenylsulfon...

~%

[1-(PHENYLSULFONYL)-1H-INDOL-2-YL]METHANOL Structure

73282-11-8

[1-(PHENYLSULFO...

chlorophenylsulfone Structure

98-09-9

chlorophenylsulfone

~%

4-(benzenesulfonyl)-3-phenylfuro[3,4-b]indole Structure

143774-52-1

4-(benzenesulfo...

3-Methylindole Structure

83-34-1

3-Methylindole

~%

4-(benzenesulfonyl)-3-phenylfuro[3,4-b]indole Structure

143774-52-1

4-(benzenesulfo...

3-Methyl-1-(phenylsulfonyl)-1H-indole Structure

58550-84-8

3-Methyl-1-(phe...

~%

4-(benzenesulfonyl)-3-phenylfuro[3,4-b]indole Structure

143774-52-1

4-(benzenesulfo...

(1-phenylsulfonyl-3-methyl-1H-indol-2-yl)(phenyl)methanone Structure

77507-53-0

(1-phenylsulfon...

~%

4-(benzenesulfonyl)-3-phenylfuro[3,4-b]indole Structure

143774-52-1

4-(benzenesulfo...

[3-methyl-1-(phenylsulfonyl)indol-2-yl]phenylmethanol Structure

143774-66-7

[3-methyl-1-(ph...

~%

4-(benzenesulfonyl)-3-phenylfuro[3,4-b]indole Structure

143774-52-1

4-(benzenesulfo...

N/A Structure

143774-67-8

N/A

~%

4-(benzenesulfonyl)-3-phenylfuro[3,4-b]indole Structure

143774-52-1

4-(benzenesulfo...


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