Tetrahedron

A new convergent synthesis of WS-5995-B, an anticoccidial antibiotic from Streptomyces auranticolor

DA Rama, DS Iyengar, M Pardhasaradhi

Index: Rama Devi; Iyengar; Pardhasaradhi Tetrahedron, 1994 , vol. 50, # 8 p. 2543 - 2550

Full Text: HTML

Citation Number: 3

Abstract

A new synthesis of WS-5995-B, an anticoccidial antibiotic isolated from Streptomyces auranticolor is reported via the coupling reaction between 3-bromo-5, 6, 7, 8- tetrahydrojuglone, and 3-methoxy-5-methyl anthranilic acid. A simple method for the preparation of the anthranilate 7 starting from p-toluidine by shorter sequence is reported.

 Related Synthetic Route
2,6-Dibromo-p-toluidine Structure

6968-24-7

2,6-Dibromo-p-t...

~%

2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid Structure

76191-52-1

2-(5-hydroxy-1,...

methyl-3-methoxy-5-methyl anthranilate Structure

115475-74-6

methyl-3-methox...

~%

2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid Structure

76191-52-1

2-(5-hydroxy-1,...

7-bromo-5,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one Structure

77199-82-7

7-bromo-5,8-dim...

~%

2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid Structure

76191-52-1

2-(5-hydroxy-1,...

7-bromo-5,8-dimethoxy-1,2,3,4-tetrahydro-1-naphthol Structure

85755-06-2

7-bromo-5,8-dim...

~%

2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid Structure

76191-52-1

2-(5-hydroxy-1,...

2-amino-3-methoxy-5-methylbenzoic acid Structure

80389-40-8

2-amino-3-metho...

~%

2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid Structure

76191-52-1

2-(5-hydroxy-1,...

p-Toluidine Structure

106-49-0

p-Toluidine

~%

2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid Structure

76191-52-1

2-(5-hydroxy-1,...

N-acetyl-2-bromo-6-methoxy p-toluidine Structure

147699-88-5

N-acetyl-2-brom...

~%

2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid Structure

76191-52-1

2-(5-hydroxy-1,...

2-Acetamido-3-methoxy-5-methylbenzoic acid Structure

147699-89-6

2-Acetamido-3-m...

~%

2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid Structure

76191-52-1

2-(5-hydroxy-1,...

3-bromo-5,6,7,8-tetrahydrojuglone Structure

1026950-14-0

3-bromo-5,6,7,8...

~%

2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid Structure

76191-52-1

2-(5-hydroxy-1,...

N/A Structure

155722-63-7

N/A

~%

2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid Structure

76191-52-1

2-(5-hydroxy-1,...

3-bromo-2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyljuglone Structure

155722-67-1

3-bromo-2-(2-me...

~%

2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid Structure

76191-52-1

2-(5-hydroxy-1,...

N/A Structure

155722-68-2

N/A

~%

2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid Structure

76191-52-1

2-(5-hydroxy-1,...

2-Acetamido-3-methoxy-5-methylbenzoic acid Structure

147699-89-6

2-Acetamido-3-m...

~94%

2-amino-3-methoxy-5-methylbenzoic acid Structure

80389-40-8

2-amino-3-metho...

2,6-Dibromo-p-toluidine Structure

6968-24-7

2,6-Dibromo-p-t...

~%

2-amino-3-methoxy-5-methylbenzoic acid Structure

80389-40-8

2-amino-3-metho...

p-Toluidine Structure

106-49-0

p-Toluidine

~%

2-amino-3-methoxy-5-methylbenzoic acid Structure

80389-40-8

2-amino-3-metho...

N-acetyl-2-bromo-6-methoxy p-toluidine Structure

147699-88-5

N-acetyl-2-brom...

~%

2-amino-3-methoxy-5-methylbenzoic acid Structure

80389-40-8

2-amino-3-metho...


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