Total Synthesis of 4′′‐<i>O</i>‐Acetylmananthoside B Part II: Synthesis of the Disaccharide Fragment

Zhao, Guilong; Yu, Zhao-Yun; Li, Yan; Pang, Li‐Na; Wang, Jianwu

doi:10.1002/cjoc.200890014

Cited by 9 publications

(5 citation statements)

References 6 publications

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“…Glycosides 11 – 18 were prepared by glycosylation of the selectively protected paromomycin derivative 19 , with donors 20 – 28 , followed by deprotection of the immediate glycosylation products 29 – 37 , as summarized in Scheme and in Table . Thioglycosides 20 , 22 , 23 , 26 , and 27 were accessed by the literature methods, while thioglycoside 21 was prepared analogously to its enantiomer 20 . Similarly, the trichloroacetimidates 24 and 28 were obtained according to the literature methods or by minor modifications thereof.…”

Section: Resultsmentioning

confidence: 99%

Influence of 4′-O-Glycoside Constitution and Configuration on Ribosomal Selectivity of Paromomycin

et al. 2015

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A series of 20 4'-O-glycosides of the aminoglycoside antibiotic paromomycin were synthesized and evaluated for their ability to inhibit protein synthesis by bacterial, mitochondrial and cytosolic ribosomes. Target selectivity, i.e., inhibition of the bacterial ribosome over eukaryotic mitochondrial and cytosolic ribosomes, which is predictive of antibacterial activity with reduced ototoxicity and systemic toxicity, was greater for the equatorial than for the axial pyranosides, and greater for the d-pentopyranosides than for the l-pentopyranosides and d-hexopyranosides. In particular, 4'-O-β-d-xylopyranosyl paromomycin shows antibacterioribosomal activity comparable to that of paromomycin, but is significantly more selective showing considerably reduced affinity for the cytosolic ribosome and for the A1555G mutant mitochondrial ribosome associated with hypersusceptibility to drug-induced ototoxicity. Compound antibacterioribosomal activity correlates with antibacterial activity, and the ribosomally more active compounds show activity against Escherichia coli, Klebsiella pneumonia, Enterobacter cloacae, Acinetobacter baumannii, and methicillin-resistant Staphylococcus aureus (MRSA). The paromomycin glycosides retain activity against clinical strains of MRSA that are resistant to paromomycin, which is demonstrated to be a consequence of 4'-O-glycosylation blocking the action of 4'-aminoglycoside nucleotidyl transferases by the use of recombinant E. coli carrying the specific resistance determinant.

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Section: Resultsmentioning

confidence: 99%

Influence of 4′-O-Glycoside Constitution and Configuration on Ribosomal Selectivity of Paromomycin

et al. 2015

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“…This greatly facilitates the investigation of structure–activity relationships. Nevertheless, the total synthesis of 1 and 2 has yet to be achieved, although work towards the synthesis of 2 has been reported by Wang and co‐workers . The outstanding cytotoxic selectivity of both 1 and 2 and their new mechanisms of action make them fascinating compounds.…”

Section: Introductionmentioning

confidence: 99%

First Total Synthesis of the Bioactive Arylnaphthyl Lignan 4‐O‐Glycosides Phyllanthusmin D and 4′′‐O‐Acetylmananthoside B

Liu¹,

Hu²,

Liu³

et al. 2017

Eur J Org Chem

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Based on the application of phase‐transfer‐catalysis and Yu glycosylations, the first total syntheses of the arylnaphthyl glycosides phyllanthusmin D and 4′′‐O‐acetylmananthoside B, which have been claimed to be ideal antitumoral lead compounds in terms of cytotoxicity, cytotoxic selectivity, and a new mechanism of action, were achieved. Starting from easily accessible compounds, the two target molecules were obtained with longest linear sequences of 9 and 15 steps, in overall yields of 29 and 9 %, respectively. As part of this synthetic investigation, an efficient and scalable synthetic route to diphyllin was established, and the atropisomeric phenomenon in the arylnaphthyl glycosides was also confirmed.

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“…[5] However, because of their nonconventional structures and the presence of a number of sterically congested, strongly electron-donating groups in one molecule, such as methoxy groups and=or methylenedioxy groups, the synthesis of polymethoxyarylnaphthalene lignans and their methylenedioxy counterparts were considerably challenging. [1][2][3][4][5][6][7][8][9] During the total synthesis of 4 00 -O-acetylmananthoside B, [10][11][12][13] unexpectedly we found a polyphosphoric acid-mediated novel reaction of succinic anhydride 3 with 1,2-dimethoxybenzene 4 to produce two polymethoxyarylnaphthalene lignans, polymethoxyarylnaphthol 1 as the minor product and polymethoxynaphtho [1,2-b]oxacycloheptatrienone 2 as the major product (Scheme 1). An optimized reaction of 3 with 4 could provide 2 specifically in good yield (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

“…3H each) 13. C NMR (CDCl 3 , 75 MHz): d 149.83, 149.81, 148.87, 148.63, 148.02, 133.97, 131.75, 128.77, 125.19, 122.12, 119.79, 113.34, 111.18, 107.03, 105.01, 100.97, 55.95, 55.71.…”

mentioning

confidence: 99%

“…ESI-MS, m=z ¼ 341.4 ([M þ H] þ ), 358.4 ([M þ NH 4 ] þ ), 698.6 ([2 M þ NH 4 ] þ ), 703.5 ([2 M þ Na] þ ). 2H) 13. C NMR (DMSO-d 6 , 100 MHz): d 168.93, 150.34, 149.87, 148.92, 148.60, 148.48, 148.27, 144.50, 141.33, 134.34, 131.87, 131.57, 127.43, 125.46, 122.23, 121.54, 121.41, 121.00, 119.20, 113.07, 112.01, 111.85, 111.60, 104.87, 101.46, 55.52, 55.48, 55.44, 55.31, 34.44.…”

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confidence: 99%

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Polyphosphoric Acid–Mediated, One-Pot, Novel Reactions to Build Polymethoxyarylnaphthalene Lignans

Zhao

Zhan

Wang

et al. 2010

Synthetic Communications

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The one-pot reaction of succinic anhydride with 1,2-dimethoxybenzene furnished two structurally complicated polymethoxyarylnaphthalene lignans, polymethoxyarylnaphthol 1 as the minor product and polymethoxynaphtho[1,2-b]oxacycloheptatrienone 2 as the major product, in the presence of a small amount of polyphosphoric acid (PPA) as catalyst at 140 C and yielded 2 as a single product in good yield when a large amount of PPA as solvent was employed at 60-80 C. The novel structures of 1 and 2 were elucidated from 1 H NMR, 13 C NMR, infrared (IR), and Electrospray ionization-mass spectrometry (ESI-MS) and further confirmed by x-ray diffractions. The possible mechanisms for the formation of 1 and 2 were also proposed.

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Total Synthesis of 4′′‐O‐Acetylmananthoside B Part II: Synthesis of the Disaccharide Fragment

Cited by 9 publications

References 6 publications

Influence of 4′-O-Glycoside Constitution and Configuration on Ribosomal Selectivity of Paromomycin

Influence of 4′-O-Glycoside Constitution and Configuration on Ribosomal Selectivity of Paromomycin

First Total Synthesis of the Bioactive Arylnaphthyl Lignan 4‐O‐Glycosides Phyllanthusmin D and 4′′‐O‐Acetylmananthoside B

Polyphosphoric Acid–Mediated, One-Pot, Novel Reactions to Build Polymethoxyarylnaphthalene Lignans

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