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

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 ...

DIMETHYL (BOC-AMINO)MALONATE Structure

DIMETHYL (BOC-A...

~88%

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

2-(tert-butoxyc...

diazomethane Structure

2-(Benzyloxy)-5-iodobenzoic acid Structure

2-(Benzyloxy)-5...

~98%

methyl 5-iodo-2-phenylmethoxybenzoate Structure

methyl 5-iodo-2...

2-(BENZYLOXY)-5-BROMOBENZALDEHYDE Structure

2-(BENZYLOXY)-5...

~%

biphenomycin A Structure

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

2-(2-benzyloxy-...

~%

biphenomycin A Structure

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

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

~%

biphenomycin A Structure

N/A Structure

~%

biphenomycin A Structure

N/A Structure

~%

biphenomycin A Structure

N/A Structure

~%

biphenomycin A Structure

N/A Structure

~%

biphenomycin A Structure

N/A Structure

~%

biphenomycin A Structure

2-(Benzyloxy)-5-iodobenzoic acid Structure

2-(Benzyloxy)-5...

~%

biphenomycin A Structure

methyl 5-iodo-2-phenylmethoxybenzoate Structure

methyl 5-iodo-2...

~%

biphenomycin A Structure

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

4,4'-bis(benzyl...

~%

biphenomycin A Structure

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

4,4'-dibenzylox...

~%

biphenomycin A Structure

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

4,4'-dibenzylox...

~%

biphenomycin A Structure

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

4,4'-dibenzylox...

~%

biphenomycin A Structure

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

4,4'-dibenzylox...

~%

biphenomycin A Structure

(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

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

~%

biphenomycin A Structure

N/A Structure

~%

biphenomycin A Structure

N/A Structure

~%

biphenomycin A Structure

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

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

~%

biphenomycin A Structure

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

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

~%

biphenomycin A Structure

N/A Structure

~%

biphenomycin A Structure

Structure

~%

biphenomycin A Structure

N/A Structure

~%

biphenomycin A Structure

Synthesis and reduction of endothiodipeptides containing mal...

[Krumme, Dirk; Tschesche, Harald Tetrahedron, 1999 , vol. 55, # 10 p. 3007 - 3018]

Application of chiral mixed phosphorus/sulfur ligands to pal...

[Matt, Thomas; Seebach, Dieter Helvetica Chimica Acta, 1998 , vol. 81, # 10 p. 1845 - 1895]