Versatile Synthesis of Acylfuranones by Reaction of Acylketenes with α??Hydroxy Ketones: Application to the One??Step Multicomponent Synthesis of Cadiolide B and …

PA Peixoto, A Boulangé, S Leleu…

Index: Peixoto, Philippe Alexandre; Boulange, Agathe; Leleu, Stephane; Franck, Xavier European Journal of Organic Chemistry, 2013 , # 16 p. 3316 - 3327

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Citation Number: 6

Abstract

Abstract Functionalized acylfuranones have been prepared in a one-step procedure by thermal fragmentation of the corresponding dioxinones in the presence of hydroxy ketones in basic conditions. Multicomponent reactions also occur on addition of an aldehyde as a third reaction partner resulting in an expeditious access to cadiolide B and its analogues.

 Related Synthetic Route
PTP inhibitor 1 Structure

2632-13-5

PTP inhibitor 1

~91%

Ethanone,2-hydroxy-1-(4-methoxyphenyl)- Structure

4136-21-4

Ethanone,2-hydr...

tert-butyl 3-(4-methoxyphenyl)-3-oxo-propanoate Structure

54441-74-6

tert-butyl 3-(4...

Acetone Structure

67-64-1

Acetone

~80%

6-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxin-4-one Structure

87769-44-6

6-(4-methoxyphe...

p-Anisic acid Structure

100-09-4

p-Anisic acid

~%

6-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxin-4-one Structure

87769-44-6

6-(4-methoxyphe...

p-Anisoyl chloride Structure

100-07-2

p-Anisoyl chloride

~%

6-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxin-4-one Structure

87769-44-6

6-(4-methoxyphe...

4,N-DIMETHOXY-N-METHYLBENZAMIDE Structure

52898-49-4

4,N-DIMETHOXY-N...

~%

6-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxin-4-one Structure

87769-44-6

6-(4-methoxyphe...

2-Methyl-2-propanyl 3-oxo-3-phenylpropanoate Structure

54441-66-6

2-Methyl-2-prop...

Acetone Structure

67-64-1

Acetone

~74%

2,2-dimethyl-6-phenyl-1,3-dioxin-4-one Structure

77092-12-7

2,2-dimethyl-6-...

benzoic acid Structure

65-85-0

benzoic acid

~%

2,2-dimethyl-6-phenyl-1,3-dioxin-4-one Structure

77092-12-7

2,2-dimethyl-6-...

Benzoyl chloride Structure

98-88-4

Benzoyl chloride

~%

2,2-dimethyl-6-phenyl-1,3-dioxin-4-one Structure

77092-12-7

2,2-dimethyl-6-...

tert-Butyl acetate Structure

540-88-5

tert-Butyl acetate

N-Methoxy-N-methylbenzamide Structure

6919-61-5

N-Methoxy-N-met...

~96%

2-Methyl-2-propanyl 3-oxo-3-phenylpropanoate Structure

54441-66-6

2-Methyl-2-prop...

benzoic acid Structure

65-85-0

benzoic acid

~%

2-Methyl-2-propanyl 3-oxo-3-phenylpropanoate Structure

54441-66-6

2-Methyl-2-prop...

Benzoyl chloride Structure

98-88-4

Benzoyl chloride

~%

2-Methyl-2-propanyl 3-oxo-3-phenylpropanoate Structure

54441-66-6

2-Methyl-2-prop...

2,2,6-Trimethyl-4H-1,3-dioxin-4-one Structure

5394-63-8

2,2,6-Trimethyl...

Benzoyl chloride Structure

98-88-4

Benzoyl chloride

~47%

2,2-dimethyl-6-phenacyl-1,3-dioxin-4-one Structure

136801-74-6

2,2-dimethyl-6-...

benzoic acid Structure

65-85-0

benzoic acid

~%

2,2-dimethyl-6-phenacyl-1,3-dioxin-4-one Structure

136801-74-6

2,2-dimethyl-6-...


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