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

Tetrahedron

Synthesis of the bacterial coenzyme methoxatin

AR Mackenzie, CJ Moody, CW Rees

Index: MacKenzie, A. Roderick; Moody, Christopher J.; Rees, Charles W. Tetrahedron, 1986 , vol. 42, # 12 p. 3259 - 3268

Full Text: HTML

Citation Number: 80

Abstract

A short total synthesis of the bacterial coenzyme methoxatin (1)(4, 5-dihydro-4, 5-dioxo-1H- pyrrolo [2, 3-f] quinoline-2, 7, 9-tricarboxylic acid) is described. The route involves the two step conversion of 4-acetamido-2-benzy1oxybenzaldehyde (5b) into methyl 6-acctamido-4- benzyloxyindole-2-carboxylate (7b)(74%), followed by regioselective annulation of the third ring (55%), and debenzylation and oxidation with benzoyl t-butyl nitroxide to give the ...

Ethanoic anhydride Structure

Ethanoic anhydride

Methyl4-aminosalicylate Structure

Methyl4-aminosa...

~96%

Methyl 4-acetamido-2-hydroxybenzoate Structure

Methyl 4-acetam...

methyl 3-(4-acetamido-2-methoxyphenyl)-2-azidopropenoate Structure

methyl 3-(4-ace...

~87%

methyl 6-acetamido-4-methoxy-1H-indole-2-carboxylate Structure

methyl 6-acetam...

Methyl 4-acetamido-2-methoxybenzoate Structure

Methyl 4-acetam...

~%

methyl 6-acetamido-4-methoxy-1H-indole-2-carboxylate Structure

methyl 6-acetam...

Methyl 4-acetamido-2-hydroxybenzoate Structure

Methyl 4-acetam...

~%

methyl 6-acetamido-4-methoxy-1H-indole-2-carboxylate Structure

methyl 6-acetam...

4-aminosalicylic acid Structure

4-aminosalicyli...

~%

methyl 6-acetamido-4-methoxy-1H-indole-2-carboxylate Structure

methyl 6-acetam...

4-acetamido-2-methoxybenzyl alcohol Structure

4-acetamido-2-m...

~%

methyl 6-acetamido-4-methoxy-1H-indole-2-carboxylate Structure

methyl 6-acetam...

Methyl4-aminosalicylate Structure

Methyl4-aminosa...

~%

methyl 6-acetamido-4-methoxy-1H-indole-2-carboxylate Structure

methyl 6-acetam...

N-(3-(benzyloxy)-4-(hydroxymethyl)phenyl)acetamide Structure

N-(3-(benzyloxy...

~99%

N-(4-formyl-3-phenylmethoxyphenyl)acetamide Structure

N-(4-formyl-3-p...

Methyl 4-acetamido-2-hydroxybenzoate Structure

Methyl 4-acetam...

~%

N-(4-formyl-3-phenylmethoxyphenyl)acetamide Structure

N-(4-formyl-3-p...

4-aminosalicylic acid Structure

4-aminosalicyli...

~%

N-(4-formyl-3-phenylmethoxyphenyl)acetamide Structure

N-(4-formyl-3-p...

methyl 4-acetamido-2-(benzyloxy)benzoate Structure

methyl 4-acetam...

~%

N-(4-formyl-3-phenylmethoxyphenyl)acetamide Structure

N-(4-formyl-3-p...

Methyl4-aminosalicylate Structure

Methyl4-aminosa...

~%

N-(4-formyl-3-phenylmethoxyphenyl)acetamide Structure

N-(4-formyl-3-p...

trimethyl 5-amino-4-methoxy-1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylate Structure

trimethyl 5-ami...

~73%

4,5-Dioxo-4,5-dihydro-1H-pyrrol[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester Structure

4,5-Dioxo-4,5-d...

Methyl 4-acetamido-2-methoxybenzoate Structure

Methyl 4-acetam...

~%

4,5-Dioxo-4,5-dihydro-1H-pyrrol[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester Structure

4,5-Dioxo-4,5-d...

Methyl 4-acetamido-2-hydroxybenzoate Structure

Methyl 4-acetam...

~%

4,5-Dioxo-4,5-dihydro-1H-pyrrol[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester Structure

4,5-Dioxo-4,5-d...

DIMETHYL TRANS-2-OXOGLUTACONATE Structure

DIMETHYL TRANS-...

~%

4,5-Dioxo-4,5-dihydro-1H-pyrrol[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester Structure

4,5-Dioxo-4,5-d...

4-aminosalicylic acid Structure

4-aminosalicyli...

~%

4,5-Dioxo-4,5-dihydro-1H-pyrrol[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester Structure

4,5-Dioxo-4,5-d...

4-acetamido-2-methoxybenzyl alcohol Structure

4-acetamido-2-m...

~%

4,5-Dioxo-4,5-dihydro-1H-pyrrol[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester Structure

4,5-Dioxo-4,5-d...

Methyl4-aminosalicylate Structure

Methyl4-aminosa...

~%

4,5-Dioxo-4,5-dihydro-1H-pyrrol[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester Structure

4,5-Dioxo-4,5-d...

Methyl 4-acetamido-2-hydroxybenzoate Structure

Methyl 4-acetam...

methyl iodide Structure

~96%

Methyl 4-acetamido-2-methoxybenzoate Structure

Methyl 4-acetam...

Mild, efficient and rapid O-debenzylation of ortho-substitut...

[Fletcher, Steven; Gunning, Patrick T. Tetrahedron Letters, 2008 , vol. 49, # 33 p. 4817 - 4819]

Mild, efficient and rapid O-debenzylation of ortho-substitut...

[Fletcher, Steven; Gunning, Patrick T. Tetrahedron Letters, 2008 , vol. 49, # 33 p. 4817 - 4819]

Mild, efficient and rapid O-debenzylation of ortho-substitut...

[Fletcher, Steven; Gunning, Patrick T. Tetrahedron Letters, 2008 , vol. 49, # 33 p. 4817 - 4819]

Mild, efficient and rapid O-debenzylation of ortho-substitut...

[Fletcher, Steven; Gunning, Patrick T. Tetrahedron Letters, 2008 , vol. 49, # 33 p. 4817 - 4819]

(S)-4-amino-5-chloro-3-iodo-2-methoxy-N-(1-azabicyclo [2.2. ...

[De Paulis, Tomas; Trivedi, Bakula L.; Zhang, Zhang-Jin; Schmidt, Dennis E.; Ebert, Michael H.; Hewlett, William A. Bioorganic and Medicinal Chemistry Letters, 1996 , vol. 6, # 22 p. 2657 - 2662]