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

Total synthesis of antibiotic hygromycin A

…, M Ohtsuka, K Nakazawa, S Ogawa

Index: Chida, Noritaka; Ohtsuka, Masami; Nakazawa, Keiichi; Ogawa, Seiichiro Journal of Organic Chemistry, 1991 , vol. 56, # 9 p. 2976 - 2983

Full Text: HTML

Citation Number: 75

Abstract

The first total synthesis of the antibiotic (-)-hygromycin A (1) has been achieved by a coupling reaction of the sugar moiety (2) and the cyclitol moiety (3). Both components were synthesized in homochiral forms starting from D-glucose. This synthesis fully confirmed the unique structure of 1, which is much different from other usual aminocyclitol antibiotics.

(3S,4R,5S,6S)-4,5-bis(benzyloxy)-6-methoxy-2-methylenetetrahydro-2H-pyran-3-ol Structure

(3S,4R,5S,6S)-4...

~%

2,3-di-O-benzyl-6-deoxy-D-arabino-5-hexulofuranose Structure

2,3-di-O-benzyl...

(3S,4R,5S,6S)-4,5-bis(benzyloxy)-6-methoxy-2-methylenetetrahydro-2H-pyran-3-ol Structure

(3S,4R,5S,6S)-4...

~%

2-acetoxy-4-methylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal Structure

2-acetoxy-4-met...

2,3-di-O-benzyl-6-deoxy-D-arabino-5-hexulofuranose Structure

2,3-di-O-benzyl...

~%

2-acetoxy-4-methylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal Structure

2-acetoxy-4-met...

methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside Structure

methyl 2,3-di-O...

~%

2-acetoxy-4-methylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal Structure

2-acetoxy-4-met...

4-(((3S,4S,5S)-5-acetyl-3,4-bis(benzyloxy)tetrahydrofuran-2-yl)oxy)-3-(benzyloxy)benzaldehyde Structure

4-(((3S,4S,5S)-...

~%

2-acetoxy-4-methylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal Structure

2-acetoxy-4-met...

(3S,4R,5S,6S)-4,5-bis(benzyloxy)-6-methoxy-2-methylenetetrahydro-2H-pyran-3-ol Structure

(3S,4R,5S,6S)-4...

~%

(3aS,4R,5S,6S,7R,7aS)-6-((E)-3-(3-acetoxy-4-(((2S,3S,4S,5S)-3,4-diacetoxy-5-(2-methyl-1,3-dioxolan-2-yl)tetrahydrofuran-2-yl)oxy)phenyl)-2-methylacrylamido)hexahydrobenzo[d][1,3]dioxole-4,5,7-triyl triacetate Structure

(3aS,4R,5S,6S,7...

2,3-di-O-benzyl-6-deoxy-D-arabino-5-hexulofuranose Structure

2,3-di-O-benzyl...

~%

(3aS,4R,5S,6S,7R,7aS)-6-((E)-3-(3-acetoxy-4-(((2S,3S,4S,5S)-3,4-diacetoxy-5-(2-methyl-1,3-dioxolan-2-yl)tetrahydrofuran-2-yl)oxy)phenyl)-2-methylacrylamido)hexahydrobenzo[d][1,3]dioxole-4,5,7-triyl triacetate Structure

(3aS,4R,5S,6S,7...

methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside Structure

methyl 2,3-di-O...

~%

(3aS,4R,5S,6S,7R,7aS)-6-((E)-3-(3-acetoxy-4-(((2S,3S,4S,5S)-3,4-diacetoxy-5-(2-methyl-1,3-dioxolan-2-yl)tetrahydrofuran-2-yl)oxy)phenyl)-2-methylacrylamido)hexahydrobenzo[d][1,3]dioxole-4,5,7-triyl triacetate Structure

(3aS,4R,5S,6S,7...

4-(((3S,4S,5S)-5-acetyl-3,4-bis(benzyloxy)tetrahydrofuran-2-yl)oxy)-3-(benzyloxy)benzaldehyde Structure

4-(((3S,4S,5S)-...

~%

(3aS,4R,5S,6S,7R,7aS)-6-((E)-3-(3-acetoxy-4-(((2S,3S,4S,5S)-3,4-diacetoxy-5-(2-methyl-1,3-dioxolan-2-yl)tetrahydrofuran-2-yl)oxy)phenyl)-2-methylacrylamido)hexahydrobenzo[d][1,3]dioxole-4,5,7-triyl triacetate Structure

(3aS,4R,5S,6S,7...

2-acetoxy-4-methylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal Structure

2-acetoxy-4-met...

~67%

2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal Structure

2-acetoxy-4-for...

(3S,4R,5S,6S)-4,5-bis(benzyloxy)-6-methoxy-2-methylenetetrahydro-2H-pyran-3-ol Structure

(3S,4R,5S,6S)-4...

~%

2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal Structure

2-acetoxy-4-for...

2,3-di-O-benzyl-6-deoxy-D-arabino-5-hexulofuranose Structure

2,3-di-O-benzyl...

~%

2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal Structure

2-acetoxy-4-for...

methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside Structure

methyl 2,3-di-O...

~%

2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal Structure

2-acetoxy-4-for...

4-(((3S,4S,5S)-5-acetyl-3,4-bis(benzyloxy)tetrahydrofuran-2-yl)oxy)-3-(benzyloxy)benzaldehyde Structure

4-(((3S,4S,5S)-...

~%

2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal Structure

2-acetoxy-4-for...

(3S,4R,5S,6S)-4,5-bis(benzyloxy)-6-methoxy-2-methylenetetrahydro-2H-pyran-3-ol Structure

(3S,4R,5S,6S)-4...

~%

2-acetoxy-4-[(E)-2-carboxy-1-propen-1-yl]phenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal Structure

2-acetoxy-4-[(E...

2,3-di-O-benzyl-6-deoxy-D-arabino-5-hexulofuranose Structure

2,3-di-O-benzyl...

~%

2-acetoxy-4-[(E)-2-carboxy-1-propen-1-yl]phenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal Structure

2-acetoxy-4-[(E...

methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside Structure

methyl 2,3-di-O...

~%

2-acetoxy-4-[(E)-2-carboxy-1-propen-1-yl]phenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal Structure

2-acetoxy-4-[(E...

4-(((3S,4S,5S)-5-acetyl-3,4-bis(benzyloxy)tetrahydrofuran-2-yl)oxy)-3-(benzyloxy)benzaldehyde Structure

4-(((3S,4S,5S)-...

~%

2-acetoxy-4-[(E)-2-carboxy-1-propen-1-yl]phenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal Structure

2-acetoxy-4-[(E...