Total Synthesis of the Biphenomycins; V. 1 Synthesis of Biphenomycin A

U Schmidt, V Leitenberger, H Griesser, J Schmidt…

Index: Schmidt; Leitenberger; Griesser; Meyer Synthesis, 1992 , # 12 p. 1248 - 1254

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Citation Number: 45

Abstract

Synthesis of Hydroxydiisotyrosine by the Enolate Method The reaction sequence is illustrated in Scheme 2. The aryl bromide 16 represents a completely protected 2-hydroxy-5- bromophenylserine and can be prepared via 15 by the Evans method. 23 The palladium (0)- catalyzed coupling of 16 with the boronic acid 17 containing an unprotected aldehyde function gives rise to the biphenyl derivative 18. The stated reaction conditions must be ...

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DIMETHYL (BOC-AMINO)MALONATE Structure

61172-70-1

DIMETHYL (BOC-A...

~88%

2-(tert-butoxycarbonylamino)-3-Methoxy-3-oxopropanoic acid Structure

61172-71-2

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diazomethane Structure

186581-53-3

diazomethane

2-(Benzyloxy)-5-iodobenzoic acid Structure

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2-(Benzyloxy)-5...

~98%

methyl 5-iodo-2-phenylmethoxybenzoate Structure

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methyl 5-iodo-2...

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2-(BENZYLOXY)-5-BROMOBENZALDEHYDE Structure

121124-94-5

2-(BENZYLOXY)-5...

~%

biphenomycin A Structure

100296-21-7

biphenomycin A

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2-(2-benzyloxy-5-bromophenyl)-[1,3]dioxane Structure

121124-96-7

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biphenomycin A Structure

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(R)-5-(2-benzyloxy-5-bromo)phenyl (S)-4-(methoxycarbonyl)oxazolidin-2-thione Structure

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(R)-5-(2-benzyl...

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biphenomycin A Structure

100296-21-7

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N/A Structure

143164-80-1

N/A

~%

biphenomycin A Structure

100296-21-7

biphenomycin A

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N/A Structure

146335-34-4

N/A

~%

biphenomycin A Structure

100296-21-7

biphenomycin A

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N/A Structure

143164-82-3

N/A

~%

biphenomycin A Structure

100296-21-7

biphenomycin A

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N/A Structure

143164-81-2

N/A

~%

biphenomycin A Structure

100296-21-7

biphenomycin A

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N/A Structure

143164-83-4

N/A

~%

biphenomycin A Structure

100296-21-7

biphenomycin A

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2-(Benzyloxy)-5-iodobenzoic acid Structure

146335-32-2

2-(Benzyloxy)-5...

~%

biphenomycin A Structure

100296-21-7

biphenomycin A

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methyl 5-iodo-2-phenylmethoxybenzoate Structure

146335-26-4

methyl 5-iodo-2...

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biphenomycin A Structure

100296-21-7

biphenomycin A

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4,4'-bis(benzyloxy)-3'-(1,3-dioxan-2-yl)-[1,1'-biphenyl]-3-carbonyl chloride Structure

146335-29-7

4,4'-bis(benzyl...

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biphenomycin A Structure

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4,4'-dibenzyloxy-3-(1,3-dioxan-2-yl)-3'-carboxybiphenyl Structure

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4,4'-dibenzylox...

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biphenomycin A Structure

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biphenomycin A

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4,4'-dibenzyloxy-3-(1,3-dioxan-2-yl)-3'-(methoxycarbonyl)biphenyl Structure

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4,4'-dibenzylox...

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biphenomycin A Structure

100296-21-7

biphenomycin A

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4,4'-dibenzyloxy-3-[(R,S)-2-(tert-butoxycarbonylamino)-2-methoxycarbonyl-1-oxoethyl]-3'-(1,3-dioxan-2-yl)biphenyl Structure

146335-30-0

4,4'-dibenzylox...

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biphenomycin A Structure

100296-21-7

biphenomycin A

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4,4'-dibenzyloxy-3-[(R)-2-(tert-butoxycarbonylamino)-2-methoxycarbonyl-(R)-1-hydroxyethyl]-3'-(1,3-dioxan-2-yl)biphenyl Structure

146335-31-1

4,4'-dibenzylox...

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biphenomycin A Structure

100296-21-7

biphenomycin A

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(3R,4S,7S,10S)-14,24-bis(benzyloxy)-10-(((benzyloxy)carbonyl)amino)-7-((R)-3-(((benzyloxy)carbonyl)amino)-2-hydroxypropyl)-3-hydroxy-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacycloundecaphane-4-carboxylic acid Structure

146388-31-0

(3R,4S,7S,10S)-...

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biphenomycin A Structure

100296-21-7

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N/A Structure

1027532-24-6

N/A

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biphenomycin A Structure

100296-21-7

biphenomycin A

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N/A Structure

143164-84-5

N/A

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biphenomycin A Structure

100296-21-7

biphenomycin A

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methyl (2S,3R)-2-((2S,4R)-5-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-4-hydroxypentanamido)-3-(4,4'-bis(benzyloxy)-3'-((S)-2-(((benzyloxy)carbonyl)amino)-3-oxo-3-(perfluorophenoxy)propyl)-[1,1'-biphenyl]-3-yl)-3-hydroxypropanoate Structure

146388-29-6

methyl (2S,3R)-...

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biphenomycin A Structure

100296-21-7

biphenomycin A

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methyl (3R,4S,7S,10S)-14,24-bis(benzyloxy)-10-(((benzyloxy)carbonyl)amino)-7-((R)-3-(((benzyloxy)carbonyl)amino)-2-hydroxypropyl)-3-hydroxy-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacycloundecaphane-4-carboxylate Structure

146388-30-9

methyl (3R,4S,7...

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biphenomycin A Structure

100296-21-7

biphenomycin A

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N/A Structure

871206-25-6

N/A

~%

biphenomycin A Structure

100296-21-7

biphenomycin A

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Structure

143164-86-7

~%

biphenomycin A Structure

100296-21-7

biphenomycin A

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N/A Structure

143164-87-8

N/A

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biphenomycin A Structure

100296-21-7

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