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

Total synthesis of hygromycin A

…, M Ohtsuka, K Nakazawa, S Ogawa

Index: Chida, Noritaka; Ohtsuka, Masami; Nakazawa, Keiichi; Ogawa, Seiichiro Journal of the Chemical Society, Chemical Communications, 1989 , # 7 p. 436 - 438

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Citation Number: 15

Abstract

The first complete synthesis of antibiotic hygromycin A is reported; coupling of the protected sugar moiety (2) and the aminocyclitol (3) derived from D-glucose as the optically active from, followed by deprotection, gives the product (1) which was identified with an aunthentic sample by 400 MHz 1H nmr spectroscopy.

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

2-acetoxy-4-met...

~%

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

2-acetoxy-4-for...

~%

(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 Structure

2-acetoxy-4-met...

~%

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

2-acetoxy-4-for...

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

2-acetoxy-4-met...

~%

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

2-acetoxy-4-for...

~%

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...

Total synthesis of antibiotic hygromycin A

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

Total synthesis of antibiotic hygromycin A

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

Total synthesis of antibiotic hygromycin A

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

Total synthesis of antibiotic hygromycin A

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