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

Tetrahedron letters

Synthesis of specifically O-alkylated anthraquinones by cycloaddition

DW Cameron, GI Feuitrill, GB Gamble, J Stavrakis

Index: Cameron, Donald W.; Feutrill, Geoffrey I.; Gamble, Glenn B.; Stavrakis, John Tetrahedron Letters, 1986 , vol. 27, # 41 p. 4999 - 5002

Full Text: HTML

Citation Number: 11

Abstract

Download full text in PDF Opens in a new window. Article suggestions will be shown in a dialog on return to ScienceDirect. ... Please enable JavaScript to use all the features on this page. ... Department of Organic Chemistry, University of Melbourne, Parkville, Vic. 3052, Australia. ... Cycloadducts from naphthoquinonoid dienophiles and 1-methoxy-1-trimethylsilyloxy butadienes undergo controlled aromatisatlon to form chiefly α-hydroxy- or ...

1-Methoxy-3-methyl-1,2-bis(trimethylsiloxy)-1,3-butadiene Structure

1-Methoxy-3-met...

3-Chloro-5,6,7-trimethoxynaphthoquinone Structure

3-Chloro-5,6,7-...

~23%

Chrysoobtusin Structure

1,2-dihydroxy-6,7,8-trimethoxy-3-methylanthracene-9,10-dione Structure

1,2-dihydroxy-6...

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(1R,4aS,9aR)-9a-chloro-1,6,7,8-tetramethoxy-3-methyl-1,2-bis((trimethylsilyl)oxy)-1,4,4a,9a-tetrahydroanthracene-9,10-dione Structure

(1R,4aS,9aR)-9a...

~%

1,2-dihydroxy-6,7,8-trimethoxy-3-methylanthracene-9,10-dione Structure

1,2-dihydroxy-6...

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(1R,4aS,9aR)-9a-chloro-8-hydroxy-1-methoxy-3-methyl-1-((trimethylsilyl)oxy)-1,4,4a,9a-tetrahydroanthracene-9,10-dione Structure

(1R,4aS,9aR)-9a...

~97%

Chrysophanic acid Structure

Chrysophanic acid

8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione Structure

8-hydroxy-1-met...

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(1R,4aR,9aS)-8-hydroxy-1-methoxy-3-methyl-1-((trimethylsilyl)oxy)-1,4,4a,9a-tetrahydroanthracene-9,10-dione Structure

(1R,4aR,9aS)-8-...

~%

Chrysophanic acid Structure

Chrysophanic acid

8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione Structure

8-hydroxy-1-met...

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Juglone Structure

~%

8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione Structure

8-hydroxy-1-met...

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2-chloro-8-hydroxynaphthalene-1,4-dione Structure

2-chloro-8-hydr...

~%

8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione Structure

8-hydroxy-1-met...

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1-Methoxy-3-methyl-1,2-bis(trimethylsiloxy)-1,3-butadiene Structure

1-Methoxy-3-met...

3-Chloro-5,6,7-trimethoxynaphthoquinone Structure

3-Chloro-5,6,7-...

~57%

Chrysoobtusin Structure

1,2-dihydroxy-6,7,8-trimethoxy-3-methylanthracene-9,10-dione Structure

1,2-dihydroxy-6...

Learn More

(1R,4aS,9aR)-9a-chloro-1,6,7,8-tetramethoxy-3-methyl-1,2-bis((trimethylsilyl)oxy)-1,4,4a,9a-tetrahydroanthracene-9,10-dione Structure

(1R,4aS,9aR)-9a...

~%

Chrysoobtusin Structure

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(1R,4aS,9aR)-9a-chloro-8-hydroxy-1-methoxy-3-methyl-1,2-bis((trimethylsilyl)oxy)-1,4,4a,9a-tetrahydroanthracene-9,10-dione Structure

(1R,4aS,9aR)-9a...

~92%

Obtusifolin Structure

1,2,8-TRIHYDROXY-3-METHYLANTHRAQUINONE Structure

1,2,8-TRIHYDROX...

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methyl 3-methyl-2-trimethylsilyloxybut-2-enoate Structure

methyl 3-methyl...

~%

1,2,8-TRIHYDROXY-3-METHYLANTHRAQUINONE Structure

1,2,8-TRIHYDROX...

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(1S,4aR,9aS)-8-hydroxy-1-methoxy-3-methyl-1,2-bis((trimethylsilyl)oxy)-1,4,4a,9a-tetrahydroanthracene-9,10-dione Structure

(1S,4aR,9aS)-8-...

~13%

Obtusifolin Structure

1,2,8-TRIHYDROXY-3-METHYLANTHRAQUINONE Structure

1,2,8-TRIHYDROX...

Learn More

1-Methoxy-3-methyl-1,2-bis(trimethylsiloxy)-1,3-butadiene Structure

1-Methoxy-3-met...

~%

1,2,8-TRIHYDROXY-3-METHYLANTHRAQUINONE Structure

1,2,8-TRIHYDROX...

Learn More

1-Methoxy-3-methyl-1,2-bis(trimethylsiloxy)-1,3-butadiene Structure

1-Methoxy-3-met...

5-hydroxy-6,7-dimethoxynaphthalene-1,4-dione Structure

5-hydroxy-6,7-d...

~71%

Obtusin Structure

Learn More

(1R,4aR,9aS)-8-hydroxy-1-methoxy-1,3-bis((trimethylsilyl)oxy)-1,4,4a,9a-tetrahydroanthracene-9,10-dione Structure

(1R,4aR,9aS)-8-...

~%

1,3,8-trihydroxyanthracene-9,10-dione Structure

1,3,8-trihydrox...

3,8-dihydroxy-1-methoxyanthracene-9,10-dione Structure

3,8-dihydroxy-1...

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(1R,4aS,9aR)-9a-chloro-8-hydroxy-1-methoxy-1,3-bis((trimethylsilyl)oxy)-1,4,4a,9a-tetrahydroanthracene-9,10-dione Structure

(1R,4aS,9aR)-9a...

~%

1,3,8-trihydroxyanthracene-9,10-dione Structure

1,3,8-trihydrox...

3,8-dihydroxy-1-methoxyanthracene-9,10-dione Structure

3,8-dihydroxy-1...

Learn More

(1R,4aS,9aR)-9a-chloro-8-hydroxy-1-methoxy-3-methyl-1-((trimethylsilyl)oxy)-1,4,4a,9a-tetrahydroanthracene-9,10-dione Structure

(1R,4aS,9aR)-9a...

~0%

Chrysophanic acid Structure

Chrysophanic acid

8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione Structure

8-hydroxy-1-met...

Learn More

Juglone Structure

~%

Chrysophanic acid Structure

Chrysophanic acid

Learn More

(1R,4aR,9aS)-8-hydroxy-1-methoxy-3-methyl-1-((trimethylsilyl)oxy)-1,4,4a,9a-tetrahydroanthracene-9,10-dione Structure

(1R,4aR,9aS)-8-...

~%

Chrysophanic acid Structure

Chrysophanic acid

8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione Structure

8-hydroxy-1-met...

Learn More

2-chloro-8-hydroxynaphthalene-1,4-dione Structure

2-chloro-8-hydr...

~%

Chrysophanic acid Structure

Chrysophanic acid

Learn More

(1R,4aS,9aR)-9a-chloro-8-hydroxy-1-methoxy-3-methyl-1,2-bis((trimethylsilyl)oxy)-1,4,4a,9a-tetrahydroanthracene-9,10-dione Structure

(1R,4aS,9aR)-9a...

~0%

Obtusifolin Structure

1,2,8-TRIHYDROXY-3-METHYLANTHRAQUINONE Structure

1,2,8-TRIHYDROX...

Learn More

methyl 3-methyl-2-trimethylsilyloxybut-2-enoate Structure

methyl 3-methyl...

~%

Obtusifolin Structure

Learn More

(1S,4aR,9aS)-8-hydroxy-1-methoxy-3-methyl-1,2-bis((trimethylsilyl)oxy)-1,4,4a,9a-tetrahydroanthracene-9,10-dione Structure

(1S,4aR,9aS)-8-...

~60%

Obtusifolin Structure

1,2,8-TRIHYDROXY-3-METHYLANTHRAQUINONE Structure

1,2,8-TRIHYDROX...

Learn More

1-Methoxy-3-methyl-1,2-bis(trimethylsiloxy)-1,3-butadiene Structure

1-Methoxy-3-met...

~%

Obtusifolin Structure

Learn More

(1R,4aR,9aS)-8-hydroxy-1-methoxy-1,3-bis((trimethylsilyl)oxy)-1,4,4a,9a-tetrahydroanthracene-9,10-dione Structure

(1R,4aR,9aS)-8-...

~%

1,3,8-trihydroxyanthracene-9,10-dione Structure

1,3,8-trihydrox...

3,8-dihydroxy-1-methoxyanthracene-9,10-dione Structure

3,8-dihydroxy-1...

Learn More

(1R,4aS,9aR)-9a-chloro-8-hydroxy-1-methoxy-1,3-bis((trimethylsilyl)oxy)-1,4,4a,9a-tetrahydroanthracene-9,10-dione Structure

(1R,4aS,9aR)-9a...

~%

1,3,8-trihydroxyanthracene-9,10-dione Structure

1,3,8-trihydrox...

3,8-dihydroxy-1-methoxyanthracene-9,10-dione Structure

3,8-dihydroxy-1...

Learn More