Tetrahedron Letters

Synthesis of coumarins by ring-closing metathesis using Grubbs' catalyst

TN Van, S Debenedetti, N De Kimpe

Index: Nguyen Van, Tuyen; Debenedetti, Silvia; De Kimpe, Norbert Tetrahedron Letters, 2003 , vol. 44, # 22 p. 4199 - 4201

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Citation Number: 82

Abstract

A novel generally applicable synthesis of coumarins from phenolic substrates utilizing ring- closing metathesis is described. This sequence involves O-allylation of phenols followed by ortho-Claisen rearrangement, subsequent based-induced isomerization affording 2-(1- propenyl) phenols, acylation with acryloyl chloride, and finally ring-closing metathesis (RCM) with Grubbs' second generation catalyst.

 Related Synthetic Route
Sesamol Structure

533-31-3

Sesamol

~%

[1,3]dioxolo[4,5-g]chromen-6-one Structure

494-56-4

[1,3]dioxolo[4,...

6-(prop-1-en-1-yl)benzo[d][1,3]dioxol-5-yl acrylate Structure

591249-43-3

6-(prop-1-en-1-...

~81%

[1,3]dioxolo[4,5-g]chromen-6-one Structure

494-56-4

[1,3]dioxolo[4,...

6-prop-2-enyl-1,3-benzodioxol-5-ol Structure

19202-23-4

6-prop-2-enyl-1...

~%

[1,3]dioxolo[4,5-g]chromen-6-one Structure

494-56-4

[1,3]dioxolo[4,...

2-propenylsesamol Structure

193757-32-3

2-propenylsesamol

~%

[1,3]dioxolo[4,5-g]chromen-6-one Structure

494-56-4

[1,3]dioxolo[4,...

Guaiacol Structure

90-05-1

Guaiacol

~%

8-METHOXYCOUMARIN Structure

2445-81-0

8-METHOXYCOUMARIN

2-methoxy-6-(prop-1-en-1-yl)phenyl acrylate Structure

591249-39-7

2-methoxy-6-(pr...

~78%

8-METHOXYCOUMARIN Structure

2445-81-0

8-METHOXYCOUMARIN

2-Methoxy-6-allylphenol Structure

579-60-2

2-Methoxy-6-all...

~%

8-METHOXYCOUMARIN Structure

2445-81-0

8-METHOXYCOUMARIN

2-Allyloxyanisole Structure

4125-43-3

2-Allyloxyanisole

~%

8-METHOXYCOUMARIN Structure

2445-81-0

8-METHOXYCOUMARIN

2-(1-Propenyl)-6-methoxyphenol Structure

1076-55-7

2-(1-Propenyl)-...

~%

8-METHOXYCOUMARIN Structure

2445-81-0

8-METHOXYCOUMARIN

2-Allyloxyanisole Structure

4125-43-3

2-Allyloxyanisole

~97%

2-Methoxy-6-allylphenol Structure

579-60-2

2-Methoxy-6-all...

2-propenylphenol Structure

6380-21-8

2-propenylphenol

Acrylyl chloride Structure

814-68-6

Acrylyl chloride

~87%

(2-prop-1-enylphenyl) prop-2-enoate Structure

151597-71-6

(2-prop-1-enylp...

(Allyloxy)benzene Structure

1746-13-0

(Allyloxy)benzene

~%

(2-prop-1-enylphenyl) prop-2-enoate Structure

151597-71-6

(2-prop-1-enylp...

2-Allylphenol Structure

1745-81-9

2-Allylphenol

~%

(2-prop-1-enylphenyl) prop-2-enoate Structure

151597-71-6

(2-prop-1-enylp...

2,5-Dimethoxyphenol Structure

18113-18-3

2,5-Dimethoxyphenol

~%

5,8-dimethoxychromen-2-one Structure

57585-52-1

5,8-dimethoxych...

2-(allyloxy)-1,4-dimethoxybenzene Structure

591249-40-0

2-(allyloxy)-1,...

~%

5,8-dimethoxychromen-2-one Structure

57585-52-1

5,8-dimethoxych...

2-allyl-3,6-dimethoxyphenol Structure

516483-78-6

2-allyl-3,6-dim...

~%

5,8-dimethoxychromen-2-one Structure

57585-52-1

5,8-dimethoxych...

2-(allyloxy)-1,4-dimethoxybenzene Structure

591249-40-0

2-(allyloxy)-1,...

~30%

2,5-dimethoxy-4-prop-2-enylphenol Structure

90377-06-3

2,5-dimethoxy-4...

2-allyl-3,6-dimethoxyphenol Structure

516483-78-6

2-allyl-3,6-dim...

2,5-Dimethoxyphenol Structure

18113-18-3

2,5-Dimethoxyphenol

~%

2,5-dimethoxy-4-prop-2-enylphenol Structure

90377-06-3

2,5-dimethoxy-4...


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