Tetrahedron

Total synthesis of maesanin and analogues

S Poigny, M Guyot, M Samadi

Index: Poigny, Stephane; Guyot, Michele; Samadi, Mohammad Tetrahedron, 1998 , vol. 54, # 49 p. 14791 - 14802

Full Text: HTML

Citation Number: 39

Abstract

An efficient total synthesis of maesanin and related quinones is reported, through direct alkylation of 1, 2, 4, 5-tetramethoxybenzene with alkylbromides, followed by oxidation with ceric ammonium nitrate (CAN) which provokes formation of the quinone and deprotection of the more hindered methyl ether in one step, to furnish the desired 2-hydroxy-5-methoxy-1, 4- benzoquinones 1a-h.

 Related Synthetic Route
1,2,4,5-tetramethoxy-3-tridecylbenzene Structure

219144-65-7

1,2,4,5-tetrame...

~54%

2-HYDROXY-5-METHOXY-3-TRIDECYL[1,4]BENZOQUINONE Structure

19833-82-0

2-HYDROXY-5-MET...

2,5-DIMETHOXY-3-TRIDECYL-[1,4]BENZOQUINONE Structure

3565-77-3

2,5-DIMETHOXY-3...

Benzene,1,2,4,5-tetramethoxy- Structure

2441-46-5

Benzene,1,2,4,5...

~%

2-HYDROXY-5-METHOXY-3-TRIDECYL[1,4]BENZOQUINONE Structure

19833-82-0

2-HYDROXY-5-MET...

2,4,5-Trimethoxybenzaldehyde Structure

4460-86-0

2,4,5-Trimethox...

~%

2-HYDROXY-5-METHOXY-3-TRIDECYL[1,4]BENZOQUINONE Structure

19833-82-0

2-HYDROXY-5-MET...

2,4,5-trimethoxyphenol Structure

20491-91-2

2,4,5-trimethox...

~%

2-HYDROXY-5-METHOXY-3-TRIDECYL[1,4]BENZOQUINONE Structure

19833-82-0

2-HYDROXY-5-MET...

1,2,4,5-tetramethoxy-3-tridecylbenzene Structure

219144-65-7

1,2,4,5-tetrame...

~%

2-HYDROXY-5-METHOXY-3-TRIDECYL[1,4]BENZOQUINONE Structure

19833-82-0

2-HYDROXY-5-MET...

(Z)-1-(2,3,5,6-tetramethoxyphenyl)-10-pentadecene Structure

219144-60-2

(Z)-1-(2,3,5,6-...

~60%

2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(10-pentadecenyl)- , (Z)- Structure

82380-21-0

2,5-Cyclohexadi...

N/A Structure

87746-51-8

N/A

1,9-Dibromononane Structure

4549-33-1

1,9-Dibromononane

~%

2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(10-pentadecenyl)- , (Z)- Structure

82380-21-0

2,5-Cyclohexadi...

15-bromopentadec-5-yne Structure

86252-57-5

15-bromopentade...

~%

2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(10-pentadecenyl)- , (Z)- Structure

82380-21-0

2,5-Cyclohexadi...

Hex-1-yne Structure

693-02-7

Hex-1-yne

~%

2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(10-pentadecenyl)- , (Z)- Structure

82380-21-0

2,5-Cyclohexadi...

Benzene,1,2,4,5-tetramethoxy- Structure

2441-46-5

Benzene,1,2,4,5...

~%

2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(10-pentadecenyl)- , (Z)- Structure

82380-21-0

2,5-Cyclohexadi...

2,4,5-Trimethoxybenzaldehyde Structure

4460-86-0

2,4,5-Trimethox...

~%

2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(10-pentadecenyl)- , (Z)- Structure

82380-21-0

2,5-Cyclohexadi...

2,4,5-trimethoxyphenol Structure

20491-91-2

2,4,5-trimethox...

~%

2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(10-pentadecenyl)- , (Z)- Structure

82380-21-0

2,5-Cyclohexadi...

15-bromopentadec-5-ene Structure

92210-93-0

15-bromopentade...

~%

2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(10-pentadecenyl)- , (Z)- Structure

82380-21-0

2,5-Cyclohexadi...

(Z)-1-(2,3,5,6-tetramethoxyphenyl)-10-pentadecene Structure

219144-60-2

(Z)-1-(2,3,5,6-...

~%

2,5-Cyclohexadiene-1,4-dione, 2-hydroxy-5-methoxy-3-(10-pentadecenyl)- , (Z)- Structure

82380-21-0

2,5-Cyclohexadi...

1,7-Dibromoheptane Structure

4549-31-9

1,7-Dibromoheptane

~%

2-hydroxy-3-[(E)-9-methoxytridec-10-en-6-yl]cyclohexa-2,5-diene-1,4-dione Structure

97987-90-1

2-hydroxy-3-[(E...

N/A Structure

80436-75-5

N/A

~%

2-hydroxy-3-[(E)-9-methoxytridec-10-en-6-yl]cyclohexa-2,5-diene-1,4-dione Structure

97987-90-1

2-hydroxy-3-[(E...

Hex-1-yne Structure

693-02-7

Hex-1-yne

~%

2-hydroxy-3-[(E)-9-methoxytridec-10-en-6-yl]cyclohexa-2,5-diene-1,4-dione Structure

97987-90-1

2-hydroxy-3-[(E...

N/A Structure

219144-62-4

N/A

~51%

2-hydroxy-3-[(E)-9-methoxytridec-10-en-6-yl]cyclohexa-2,5-diene-1,4-dione Structure

97987-90-1

2-hydroxy-3-[(E...

N/A Structure

99621-95-1

N/A

Benzene,1,2,4,5-tetramethoxy- Structure

2441-46-5

Benzene,1,2,4,5...

~%

2-hydroxy-3-[(E)-9-methoxytridec-10-en-6-yl]cyclohexa-2,5-diene-1,4-dione Structure

97987-90-1

2-hydroxy-3-[(E...

2,4,5-Trimethoxybenzaldehyde Structure

4460-86-0

2,4,5-Trimethox...

~%

2-hydroxy-3-[(E)-9-methoxytridec-10-en-6-yl]cyclohexa-2,5-diene-1,4-dione Structure

97987-90-1

2-hydroxy-3-[(E...

2,4,5-trimethoxyphenol Structure

20491-91-2

2,4,5-trimethox...

~%

2-hydroxy-3-[(E)-9-methoxytridec-10-en-6-yl]cyclohexa-2,5-diene-1,4-dione Structure

97987-90-1

2-hydroxy-3-[(E...

1-bromo-(Z)-8-tridecene Structure

135062-21-4

1-bromo-(Z)-8-t...

~%

2-hydroxy-3-[(E)-9-methoxytridec-10-en-6-yl]cyclohexa-2,5-diene-1,4-dione Structure

97987-90-1

2-hydroxy-3-[(E...

N/A Structure

219144-62-4

N/A

~%

2-hydroxy-3-[(E)-9-methoxytridec-10-en-6-yl]cyclohexa-2,5-diene-1,4-dione Structure

97987-90-1

2-hydroxy-3-[(E...

15-bromopentadec-5-yne Structure

86252-57-5

15-bromopentade...

~%

15-bromopentadec-5-ene Structure

92210-93-0

15-bromopentade...

1,9-Dibromononane Structure

4549-33-1

1,9-Dibromononane

~%

15-bromopentadec-5-ene Structure

92210-93-0

15-bromopentade...

Hex-1-yne Structure

693-02-7

Hex-1-yne

~%

15-bromopentadec-5-ene Structure

92210-93-0

15-bromopentade...


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