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

Tetrahedron

Reactions of ketene acetals-14 The use of simple mixed vinylketene acetals in the annulation of quinones

J Savard, P Brassard

Index: Savard, Jacques; Brassard, Paul Tetrahedron, 1984 , vol. 40, # 18 p. 3455 - 3464

Full Text: HTML

Citation Number: 157

Abstract

α, β-β, γ-unsaturated esters can be converted by strong base and chlorotrimethylsilane to the corresponding mixed vinylketene acetals which are shown to be particularly useful and generally applicable reagents for the regiospecific annulation of halogenoquinones. The reaction proceeds readily with a variety of substrates including benzoquinones.

2-Chloro-1,4-naphthoquinone Structure

2-Chloro-1,4-na...

1,2-dimethoxy-1-trimethylsilyloxy-1,3-butadiene Structure

1,2-dimethoxy-1...

~3%

1-Hydroxy-2-Methoxyanthraquinone Structure

1-Hydroxy-2-Met...

1,2-Dimethoxyanthracene-9,10-dione Structure

1,2-Dimethoxyan...

chlorojuglone Structure

(1-methoxy-2-methylbuta-1,3-dienoxy)-trimethylsilane Structure

(1-methoxy-2-me...

~32%

1,5-dihydroxy-2-methylanthracene-9,10-dione Structure

1,5-dihydroxy-2...

N/A Structure

crotyl bromide Structure

Methyl chloroformate Structure

Methyl chloroformate

~60%

3-Butenoic acid, 2-Methyl-, Methyl ester Structure

3-Butenoic acid...

2,6-DICHLORO-1,4-BENZOQUINONE Structure

2,6-DICHLORO-1,...

Brassard's diene Structure

Brassard's diene

~5%

2-Chloro-8-hydroxy-6-methoxy-1,4-naphthoquinone Structure

2-Chloro-8-hydr...

2-chloro-6,8-dimethoxynaphthalene-1,4-dione Structure

2-chloro-6,8-di...

N/A Structure

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane Structure

(1-methoxy-3-me...

~82%

9,10-Anthracenedione,1,5,8-trihydroxy-3- methyl- Structure

9,10-Anthracene...

1,4-dihydroxy-8-methoxy-6-methylanthraquinone Structure

1,4-dihydroxy-8...

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

2-chloro-8-hydr...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane Structure

(1-methoxy-3-me...

~3%

Chrysophanic acid Structure

Chrysophanic acid

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

8-hydroxy-1-met...

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

2-chloro-8-hydr...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane Structure

(1-methoxy-3-me...

~3%

Chrysophanic acid Structure

Chrysophanic acid

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

8-hydroxy-1-met...

Detail

3-chloro-5-methoxy-1,4-naphthoquinone Structure

3-chloro-5-meth...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane Structure

(1-methoxy-3-me...

~43%

8-Methyl Chrysophanol Structure

8-Methyl Chryso...

1,8-DIMETHOXY-3-METHYLANTHRAQUINONE Structure

1,8-DIMETHOXY-3...

3-chloro-5-methoxy-1,4-naphthoquinone Structure

3-chloro-5-meth...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane Structure

(1-methoxy-3-me...

~49%

8-Methyl Chrysophanol Structure

8-Methyl Chryso...

1,8-DIMETHOXY-3-METHYLANTHRAQUINONE Structure

1,8-DIMETHOXY-3...

2-chloro-8-hydroxy-6-methyl-1,4-naphthoquinone Structure

2-chloro-8-hydr...

Brassard's diene Structure

Brassard's diene

~9%

Physcion Structure

1-Hydroxy-3,8-dimethoxy-6-methylanthraquinone Structure

1-Hydroxy-3,8-d...

2-Chloro-1,4-naphthoquinone Structure

2-Chloro-1,4-na...

Brassard's diene Structure

Brassard's diene

~99%

1-Hydroxy-3-methoxy-9,10-anthraquinone Structure

1-Hydroxy-3-met...

chlorojuglone Structure

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane Structure

(1-methoxy-3-me...

~56%

1,5-Dihydroxy-3-methylanthraquinone Structure

1,5-Dihydroxy-3...

2-Chloro-8-hydroxy-6-methoxy-1,4-naphthoquinone Structure

2-Chloro-8-hydr...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane Structure

(1-methoxy-3-me...

~66%

Physcion Structure

1-hydroxy-6,8-dimethoxy-3-methylanthracene-9,10-dione Structure

1-hydroxy-6,8-d...

Detail

2-chloro-8-hydroxy-6-methyl-1,4-naphthoquinone Structure

2-chloro-8-hydr...

Brassard's diene Structure

Brassard's diene

~73%

Physcion Structure

1-Hydroxy-3,8-dimethoxy-6-methylanthraquinone Structure

1-Hydroxy-3,8-d...

2-Chloro-8-hydroxy-6-methoxy-1,4-naphthoquinone Structure

2-Chloro-8-hydr...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane Structure

(1-methoxy-3-me...

~8%

Physcion Structure

1-hydroxy-6,8-dimethoxy-3-methylanthracene-9,10-dione Structure

1-hydroxy-6,8-d...

Detail

2-Chloro-1,4-naphthoquinone Structure

2-Chloro-1,4-na...

1,2-dimethoxy-1-trimethylsilyloxy-1,3-butadiene Structure

1,2-dimethoxy-1...

~75%

1-Hydroxy-2-Methoxyanthraquinone Structure

1-Hydroxy-2-Met...

1,2-Dimethoxyanthracene-9,10-dione Structure

1,2-Dimethoxyan...

2-Chloro-1,4-naphthoquinone Structure

2-Chloro-1,4-na...

(1-methoxy-2-methylbuta-1,3-dienoxy)-trimethylsilane Structure

(1-methoxy-2-me...

~54%

1-Hydroxy-2-methylanthraquinone Structure

1-Hydroxy-2-met...

N/A Structure

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

2-chloro-8-hydr...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane Structure

(1-methoxy-3-me...

~21%

Chrysophanic acid Structure

Chrysophanic acid

N/A Structure

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

2-chloro-8-hydr...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane Structure

(1-methoxy-3-me...

~64%

Chrysophanic acid Structure

Chrysophanic acid

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

8-hydroxy-1-met...

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

2-chloro-8-hydr...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane Structure

(1-methoxy-3-me...

~62%

Chrysophanic acid Structure

Chrysophanic acid

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

8-hydroxy-1-met...

Detail

2-Chloro-1,4-naphthoquinone Structure

2-Chloro-1,4-na...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane Structure

(1-methoxy-3-me...

~92%

Pachybasin Structure

N/A Structure

2,6-DICHLORO-1,4-BENZOQUINONE Structure

2,6-DICHLORO-1,...

Brassard's diene Structure

Brassard's diene

~92%

2-Chloro-8-hydroxy-6-methoxy-1,4-naphthoquinone Structure

2-Chloro-8-hydr...

2-chloro-6,8-dimethoxynaphthalene-1,4-dione Structure

2-chloro-6,8-di...

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

2-chloro-8-hydr...

Brassard's diene Structure

Brassard's diene

~53%

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

1,8-dihydroxy-3...

2-chloro-5-methoxycyclohexa-2,5-diene-1,4-dione Structure

2-chloro-5-meth...

Brassard's diene Structure

Brassard's diene

~20%

5-hydroxy-2,7-dimethoxy-naphthalene-1,4-dione Structure

5-hydroxy-2,7-d...

5-hydroxy-2,7-dimethoxy-naphthalene-1,4-dione Structure

5-hydroxy-2,7-d...

methyl iodide Structure

~%

2,5,7-TRIMETHOXY-[1,4]NAPHTHOQUINONE Structure

2,5,7-TRIMETHOX...

Preparation of anthraquinones from 10-hydroxy-9-anthraceneca...

[Bhawal, Baburao M.; Khanapure, Subhash P.; Zhang, Hongming; Biehl, Edward R. Journal of Organic Chemistry, 1991 , vol. 56, # 8 p. 2846 - 2849]

Obtention of Anthraquinones by Selective Oxidation of the Co...

[Anastasia; Allevi; Bettini; Fiecchi; Sanvito Synthesis, 1990 , # 11 p. 1083 - 1084]

Obtention of Anthraquinones by Selective Oxidation of the Co...

[Anastasia; Allevi; Bettini; Fiecchi; Sanvito Synthesis, 1990 , # 11 p. 1083 - 1084]

Monoketale von 1.2??Diketonen. Ein Beitrag zur Theorie der B...

[Kuhn,R.; Trischmann,H. Chemische Berichte, 1961 , vol. 94, p. 2258 - 2263]

Monoketale von 1.2??Diketonen. Ein Beitrag zur Theorie der B...

[Kuhn,R.; Trischmann,H. Chemische Berichte, 1961 , vol. 94, p. 2258 - 2263]