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

The Journal of organic chemistry

Total synthesis of dimethyl sulfomycinamate

TR Kelly, F Lang

Index: Kelly, T. Ross; Lang, Fengrui Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4623 - 4633

Full Text: HTML

Citation Number: 120

Abstract

Dimethyl sulfomycinamate (1), a methanolysis product from the natural antibiotic sulfomycin I, is synthesized in 11 steps (Scheme 19). The chemistry of various pyridine, thiazole, and oxazole heterocycles and their coupling reactions under palladium catalysis are examined. The key transformations in the synthesis are the selective palladium-catalyzed coupling reactions on doubly activated pyridine 62 and the condensation reaction between bromo ...

2-Bromo-3-methoxy-6-methylpyridine Structure

2-Bromo-3-metho...

~74%

2-Bromo-3-methoxypyridine-6-carboxylic acid Structure

2-Bromo-3-metho...

Methyl 6-bromo-5-methoxy-2-pyridinecarboxylate Structure

Methyl 6-bromo-...

~93%

methyl 6-bromo-5-hydroxy-2-pyridinecarboxylate Structure

methyl 6-bromo-...

diazomethane Structure

6-bromo-5-hydroxy-2-pyridinecarboxylic acid Structure

6-bromo-5-hydro...

~42%

methyl 6-bromo-5-hydroxy-2-pyridinecarboxylate Structure

methyl 6-bromo-...

Methyl 6-bromo-5-methoxy-2-pyridinecarboxylate Structure

Methyl 6-bromo-...

2-Amino-6-picoline Structure

2-Amino-6-picoline

~%

6-Acetamidopyridine-2-carboxylic acid Structure

6-Acetamidopyri...

TRIMETHYL(PHENYL)TIN Structure

TRIMETHYL(PHENYL)TIN

N/A Structure

~89%

2-(4-methoxyphenyl)-4-phenyl-1,3-oxazole Structure

2-(4-methoxyphe...

4-Methoxybenzamide Structure

4-Methoxybenzamide

~%

2-(4-methoxyphenyl)-4-phenyl-1,3-oxazole Structure

2-(4-methoxyphe...

2-(4-methoxy-phenyl)-oxazol-4-one Structure

2-(4-methoxy-ph...

~%

2-(4-methoxyphenyl)-4-phenyl-1,3-oxazole Structure

2-(4-methoxyphe...

Methyl 6-bromo-5-methoxy-2-pyridinecarboxylate Structure

Methyl 6-bromo-...

~96%

6-bromo-5-hydroxy-2-pyridinecarboxylic acid Structure

6-bromo-5-hydro...

6-Methyl-3-pyridinol Structure

6-Methyl-3-pyridinol

~%

6-bromo-5-hydroxy-2-pyridinecarboxylic acid Structure

6-bromo-5-hydro...

2-Bromo-3-methoxy-6-methylpyridine Structure

2-Bromo-3-metho...

~%

6-bromo-5-hydroxy-2-pyridinecarboxylic acid Structure

6-bromo-5-hydro...

2-Bromo-6-methylpyridin-3-ol Structure

2-Bromo-6-methy...

~%

6-bromo-5-hydroxy-2-pyridinecarboxylic acid Structure

6-bromo-5-hydro...

2-Bromo-3-methoxypyridine-6-carboxylic acid Structure

2-Bromo-3-metho...

~%

6-bromo-5-hydroxy-2-pyridinecarboxylic acid Structure

6-bromo-5-hydro...

Total synthesis of dimethyl sulfomycinamate

[Journal of Organic Chemistry, , vol. 61, # 14 p. 4623 - 4633]

Total synthesis of dimethyl sulfomycinamate

[Journal of Organic Chemistry, , vol. 61, # 14 p. 4623 - 4633]