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

Tetrahedron

A synthetic road to the forest of strychnos, aspidosperma, schizozygane and eburnamine alkaloids by way of the novel photoisomerization

Y Ban, K Yoshida, J Goto, T Oishi, E Takeda

Index: Ban, Yoshio; Yoshida, Kiyoshi; Goto, Jiro; Oishi, Takeshi; Takeda, Eiko; Ishigamori Tetrahedron, 1983 , vol. 39, # 22 p. 3657 - 3668

Full Text: HTML

Citation Number: 59

Abstract

The novel photoisomerization of 1-acylindoles accompanied by a conversion of indole to indolenine afforded 3-acylindolenines, a so far unknown reactive species, as a major product. This reaction was thorougly investigated and applied with success to the total synthesis of Strychnos, Aspidosperma, Schizozygane and Eburnamine alkaloids through a versatile intermediate 9-membered ring system, synthesized in a one pot reaction by ...

1,2,3,4,5,6,7,8-octahydroazonino[5,4-b]indole Structure

1,2,3,4,5,6,7,8...

2-Chlorobutyryl Chloride Structure

2-Chlorobutyryl...

~90%

2-chloro-1-(2,4,5,6,7,8-hexahydro-1H-azonino[5,4-b]indol-3-yl)butan-1-one Structure

2-chloro-1-(2,4...

Methyl 5-chloro-5-oxopentanoate Structure

Methyl 5-chloro...

~%

2-chloro-1-(2,4,5,6,7,8-hexahydro-1H-azonino[5,4-b]indol-3-yl)butan-1-one Structure

2-chloro-1-(2,4...

Nonanedioic acid,5-oxo- Structure

Nonanedioic aci...

~%

2-chloro-1-(2,4,5,6,7,8-hexahydro-1H-azonino[5,4-b]indol-3-yl)butan-1-one Structure

2-chloro-1-(2,4...

2,3,5,6,7,8-hexahydro-1H-azonino[5,4-b]indol-4-one Structure

2,3,5,6,7,8-hex...

~%

2-chloro-1-(2,4,5,6,7,8-hexahydro-1H-azonino[5,4-b]indol-3-yl)butan-1-one Structure

2-chloro-1-(2,4...

3-(6-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)propanoyl chloride Structure

3-(6-oxo-6,7,8,...

~%

2-chloro-1-(2,4,5,6,7,8-hexahydro-1H-azonino[5,4-b]indol-3-yl)butan-1-one Structure

2-chloro-1-(2,4...

3-(6-Oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl)-propionyl azide Structure

3-(6-Oxo-6,7,8,...

~%

2-chloro-1-(2,4,5,6,7,8-hexahydro-1H-azonino[5,4-b]indol-3-yl)butan-1-one Structure

2-chloro-1-(2,4...

benzyl (2-(6-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)ethyl)carbamate Structure

benzyl (2-(6-ox...

~%

2-chloro-1-(2,4,5,6,7,8-hexahydro-1H-azonino[5,4-b]indol-3-yl)butan-1-one Structure

2-chloro-1-(2,4...

10-(aminomethyl)-8,9-dihydro-7H-pyrido[1,2-a]indol-6-one Structure

10-(aminomethyl...

~43%

2,3-Dihydro-1H-carbazol-4(9H)-one Structure

2,3-Dihydro-1H-...

Ethanone,1-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)- Structure

Ethanone,1-(1,2...

~3%

1-(6,7,8,9-tetrahydro-5H-carbazol-2-yl)ethanone Structure

1-(6,7,8,9-tetr...

1-(2,3,9,9a-tetrahydro-1H-carbazol-4-yl)ethanone Structure

1-(2,3,9,9a-tet...

1-(6,7,8,9-tetrahydro-5H-carbazol-4-yl)ethanone Structure

1-(6,7,8,9-tetr...

Detail

N/A Structure

~78%

4-(2-aminoethyl)-2,3-dihydropyrrolo[1,2-a]indol-1-one Structure

4-(2-aminoethyl...

Diethyl 4-oxoheptanedioate Structure

Diethyl 4-oxohe...

~%

4-(2-aminoethyl)-2,3-dihydropyrrolo[1,2-a]indol-1-one Structure

4-(2-aminoethyl...

(3-Oxo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-acetyl chloride Structure

(3-Oxo-2,3-dihy...

~%

4-(2-aminoethyl)-2,3-dihydropyrrolo[1,2-a]indol-1-one Structure

4-(2-aminoethyl...

2-(1-oxo-2,3-dihydropyrrolo[1,2-a]indol-4-yl)acetic acid Structure

2-(1-oxo-2,3-di...

~%

4-(2-aminoethyl)-2,3-dihydropyrrolo[1,2-a]indol-1-one Structure

4-(2-aminoethyl...

2-(1-oxo-2,3-dihydropyrrolo[1,2-a]indol-4-yl)acetamide Structure

2-(1-oxo-2,3-di...

~%

4-(2-aminoethyl)-2,3-dihydropyrrolo[1,2-a]indol-1-one Structure

4-(2-aminoethyl...

Phenylhydrazine Structure

Phenylhydrazine

~%

4-(2-aminoethyl)-2,3-dihydropyrrolo[1,2-a]indol-1-one Structure

4-(2-aminoethyl...

benzyl (2-(6-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)ethyl)carbamate Structure

benzyl (2-(6-ox...

~%

10-(2-aminoethyl)-8,9-dihydro-7H-pyrido[1,2-a]indol-6-one Structure

10-(2-aminoethy...

Methyl 5-chloro-5-oxopentanoate Structure

Methyl 5-chloro...

~%

10-(2-aminoethyl)-8,9-dihydro-7H-pyrido[1,2-a]indol-6-one Structure

10-(2-aminoethy...

Nonanedioic acid,5-oxo- Structure

Nonanedioic aci...

~%

10-(2-aminoethyl)-8,9-dihydro-7H-pyrido[1,2-a]indol-6-one Structure

10-(2-aminoethy...

Ethanone,1-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)- Structure

Ethanone,1-(1,2...

~11%

1-(6,7,8,9-tetrahydro-5H-carbazol-2-yl)ethanone Structure

1-(6,7,8,9-tetr...

1-(2,3,9,9a-tetrahydro-1H-carbazol-4-yl)ethanone Structure

1-(2,3,9,9a-tet...

1-(6,7,8,9-tetrahydro-5H-carbazol-4-yl)ethanone Structure

1-(6,7,8,9-tetr...

Detail

Methyl 5-chloro-5-oxopentanoate Structure

Methyl 5-chloro...

~%

3-benzoyl-1,2,5,6,7,8-hexahydroazonino[5,4-b]indol-4-one Structure

3-benzoyl-1,2,5...

Nonanedioic acid,5-oxo- Structure

Nonanedioic aci...

~%

3-benzoyl-1,2,5,6,7,8-hexahydroazonino[5,4-b]indol-4-one Structure

3-benzoyl-1,2,5...

3-(6-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)propanoyl chloride Structure

3-(6-oxo-6,7,8,...

~%

3-benzoyl-1,2,5,6,7,8-hexahydroazonino[5,4-b]indol-4-one Structure

3-benzoyl-1,2,5...

3-(6-Oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl)-propionyl azide Structure

3-(6-Oxo-6,7,8,...

~%

3-benzoyl-1,2,5,6,7,8-hexahydroazonino[5,4-b]indol-4-one Structure

3-benzoyl-1,2,5...

benzyl (2-(6-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)ethyl)carbamate Structure

benzyl (2-(6-ox...

~%

3-benzoyl-1,2,5,6,7,8-hexahydroazonino[5,4-b]indol-4-one Structure

3-benzoyl-1,2,5...

3-(6-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)propanoyl chloride Structure

3-(6-oxo-6,7,8,...

~%

10-(2-aminoethyl)-8,9-dihydro-7H-pyrido[1,2-a]indol-6-one Structure

10-(2-aminoethy...

3-(6-Oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl)-propionyl azide Structure

3-(6-Oxo-6,7,8,...

~%

10-(2-aminoethyl)-8,9-dihydro-7H-pyrido[1,2-a]indol-6-one Structure

10-(2-aminoethy...

1,2,5,6-tetrahydro-4H,7H-3,12b-methanoazepino[3,4,5-hi]benzo[b]indolizin-7-one Structure

1,2,5,6-tetrahy...

~%

ctk2h1149 Structure

2,3,4,4a,5,6-hexahydroazepino[3,4,5-hi]benzo[b]indolizin-7(1H)-one Structure

2,3,4,4a,5,6-he...

~21%

ctk2h1149 Structure

Ethanone,1-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)- Structure

Ethanone,1-(1,2...

~6%

1-(6,7,8,9-tetrahydro-5H-carbazol-2-yl)ethanone Structure

1-(6,7,8,9-tetr...

1-(2,3,9,9a-tetrahydro-1H-carbazol-4-yl)ethanone Structure

1-(2,3,9,9a-tet...

1-(6,7,8,9-tetrahydro-5H-carbazol-4-yl)ethanone Structure

1-(6,7,8,9-tetr...

Detail

5-Ketoenanthic acid methyl ester Structure

5-Ketoenanthic ...

~%

4a-methyl-2,3-dihydro-1H-carbazol-4-one Structure

4a-methyl-2,3-d...

Phenylhydrazine Structure

Phenylhydrazine

~%

4a-methyl-2,3-dihydro-1H-carbazol-4-one Structure

4a-methyl-2,3-d...

4a-methyl-2,3-dihydro-1H-carbazol-4-one Structure

4a-methyl-2,3-d...

~25%

4a-methyl-1,2,3,4,9,9a-hexahydrocarbazol-4-ol Structure

4a-methyl-1,2,3...

10-Methyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-one Structure

10-Methyl-8,9-d...

~%

4a-methyl-1,2,3,4,9,9a-hexahydrocarbazol-4-ol Structure

4a-methyl-1,2,3...

5-Ketoenanthic acid methyl ester Structure

5-Ketoenanthic ...

~%

4a-methyl-1,2,3,4,9,9a-hexahydrocarbazol-4-ol Structure

4a-methyl-1,2,3...

Phenylhydrazine Structure

Phenylhydrazine

~%

4a-methyl-1,2,3,4,9,9a-hexahydrocarbazol-4-ol Structure

4a-methyl-1,2,3...

4-oxosuberic acid Structure

4-oxosuberic acid

~%

2-(6-oxo-8,9-dihydro-7H-pyrido[1,2-a]indol-10-yl)acetic acid Structure

2-(6-oxo-8,9-di...

Phenylhydrazine Structure

Phenylhydrazine

~%

2-(6-oxo-8,9-dihydro-7H-pyrido[1,2-a]indol-10-yl)acetic acid Structure

2-(6-oxo-8,9-di...

Methyl 5-chloro-5-oxopentanoate Structure

Methyl 5-chloro...

~%

3-(6-oxo-8,9-dihydro-7H-pyrido[1,2-a]indol-10-yl)propanoic acid Structure

3-(6-oxo-8,9-di...

Nonanedioic acid,5-oxo- Structure

Nonanedioic aci...

~%

3-(6-oxo-8,9-dihydro-7H-pyrido[1,2-a]indol-10-yl)propanoic acid Structure

3-(6-oxo-8,9-di...

Diethyl 4-oxoheptanedioate Structure

Diethyl 4-oxohe...

Phenylhydrazine Structure

Phenylhydrazine

~%

2-(1-oxo-2,3-dihydropyrrolo[1,2-a]indol-4-yl)acetic acid Structure

2-(1-oxo-2,3-di...

(3-Oxo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-acetyl chloride Structure

(3-Oxo-2,3-dihy...

~95%

2-(1-oxo-2,3-dihydropyrrolo[1,2-a]indol-4-yl)acetamide Structure

2-(1-oxo-2,3-di...

Diethyl 4-oxoheptanedioate Structure

Diethyl 4-oxohe...

~%

2-(1-oxo-2,3-dihydropyrrolo[1,2-a]indol-4-yl)acetamide Structure

2-(1-oxo-2,3-di...

2-(1-oxo-2,3-dihydropyrrolo[1,2-a]indol-4-yl)acetic acid Structure

2-(1-oxo-2,3-di...

~%

2-(1-oxo-2,3-dihydropyrrolo[1,2-a]indol-4-yl)acetamide Structure

2-(1-oxo-2,3-di...

Phenylhydrazine Structure

Phenylhydrazine

~%

2-(1-oxo-2,3-dihydropyrrolo[1,2-a]indol-4-yl)acetamide Structure

2-(1-oxo-2,3-di...

10-(2-aminoethyl)-8,9-dihydro-7H-pyrido[1,2-a]indol-6-one Structure

10-(2-aminoethy...

~88%

2,3,5,6,7,8-hexahydro-1H-azonino[5,4-b]indol-4-one Structure

2,3,5,6,7,8-hex...

Methyl 5-chloro-5-oxopentanoate Structure

Methyl 5-chloro...

~%

2,3,5,6,7,8-hexahydro-1H-azonino[5,4-b]indol-4-one Structure

2,3,5,6,7,8-hex...

Nonanedioic acid,5-oxo- Structure

Nonanedioic aci...

~%

2,3,5,6,7,8-hexahydro-1H-azonino[5,4-b]indol-4-one Structure

2,3,5,6,7,8-hex...

3-(6-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)propanoyl chloride Structure

3-(6-oxo-6,7,8,...

~%

2,3,5,6,7,8-hexahydro-1H-azonino[5,4-b]indol-4-one Structure

2,3,5,6,7,8-hex...

3-(6-Oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl)-propionyl azide Structure

3-(6-Oxo-6,7,8,...

~%

2,3,5,6,7,8-hexahydro-1H-azonino[5,4-b]indol-4-one Structure

2,3,5,6,7,8-hex...

benzyl (2-(6-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)ethyl)carbamate Structure

benzyl (2-(6-ox...

~%

2,3,5,6,7,8-hexahydro-1H-azonino[5,4-b]indol-4-one Structure

2,3,5,6,7,8-hex...

6-oxo-10-(N-benzyl-2-aminoethyl)-6,7,8,9-tetrahydro-pyrido(1,2-a)indole Structure

6-oxo-10-(N-ben...

~34%

3-benzyl-1,2,5,6,7,8-hexahydroazonino[5,4-b]indol-4-one Structure

3-benzyl-1,2,5,...

Methyl 5-chloro-5-oxopentanoate Structure

Methyl 5-chloro...

~%

3-benzyl-1,2,5,6,7,8-hexahydroazonino[5,4-b]indol-4-one Structure

3-benzyl-1,2,5,...

Nonanedioic acid,5-oxo- Structure

Nonanedioic aci...

~%

3-benzyl-1,2,5,6,7,8-hexahydroazonino[5,4-b]indol-4-one Structure

3-benzyl-1,2,5,...

3-(6-oxo-8,9-dihydro-7H-pyrido[1,2-a]indol-10-yl)propanoic acid Structure

3-(6-oxo-8,9-di...

~%

3-benzyl-1,2,5,6,7,8-hexahydroazonino[5,4-b]indol-4-one Structure

3-benzyl-1,2,5,...

3-(6-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)propanoyl chloride Structure

3-(6-oxo-6,7,8,...

~%

3-benzyl-1,2,5,6,7,8-hexahydroazonino[5,4-b]indol-4-one Structure

3-benzyl-1,2,5,...

3-(6-Oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl)-propionyl azide Structure

3-(6-Oxo-6,7,8,...

~%

3-benzyl-1,2,5,6,7,8-hexahydroazonino[5,4-b]indol-4-one Structure

3-benzyl-1,2,5,...

benzyl (2-(6-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)ethyl)carbamate Structure

benzyl (2-(6-ox...

~%

3-benzyl-1,2,5,6,7,8-hexahydroazonino[5,4-b]indol-4-one Structure

3-benzyl-1,2,5,...

10-(2-aminoethyl)-8,9-dihydro-7H-pyrido[1,2-a]indol-6-one Structure

10-(2-aminoethy...

~%

3-benzyl-1,2,5,6,7,8-hexahydroazonino[5,4-b]indol-4-one Structure

3-benzyl-1,2,5,...

Novel photoisomerization of 1-acylindoles to 3-acylindolenin...

[Ban, Yoshio; Yoshida, Kiyoshi; Goto, Jiro; Oishi, Takeshi Journal of the American Chemical Society, 1981 , vol. 103, # 23 p. 6990 - 6992]

Novel photoisomerization of 1-acylindoles to 3-acylindolenin...

[Ban, Yoshio; Yoshida, Kiyoshi; Goto, Jiro; Oishi, Takeshi Journal of the American Chemical Society, 1981 , vol. 103, # 23 p. 6990 - 6992]

Novel photoisomerization of 1-acylindoles to 3-acylindolenin...

[Ban, Yoshio; Yoshida, Kiyoshi; Goto, Jiro; Oishi, Takeshi Journal of the American Chemical Society, 1981 , vol. 103, # 23 p. 6990 - 6992]