A new synthesis of (–)-anisomycin and its demethoxy analogue from<scp>D</scp>-ribose

Buchanan, J. G.; MacLean, Keith A.; Wightman, R. H.; Paulsen, Hans

doi:10.1039/p19850001463

Cited by 29 publications

(14 citation statements)

References 5 publications

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“…Presumably the bulky benzyl group at C-2 hinders the elimination process, rendering the less reactive reagents inactive. Failure of the more reactive reagents (which led to decomposition) was probably a result of reaction at, and elimination of, the C-4 hydroxyl or intramolecular attack of the free C-4 hydroxyl on the C-1 nitrile or the activated oxime (16).…”

Section: Resultsmentioning

confidence: 99%

The synthesis of protected 5-azido-5-deoxy-D-glucononitriles as precursors of glycosidase inhibitors

Bird¹,

Dolphin²,

Withers³

1990

Can. J. Chem.

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The successful syntheses of 5-azido-2,3,4,6-tetra-O-benzyl-5-deoxy-~-glucononitrile and 2,3,4,6-tetra-0-benzyl-5-deoxy-5-trifluoroacetarnido-D-glucononitrile starting from D-glucose are described. Unsuccessful attempts were made to convert these two compounds into a protected 5-amino-5-deoxy-D-glucononitrile and to subsequently cyclize them to an amidine analogue of glucose as a possible glycosidase inhibitor. On dCcrit des synthkses rCalisables des 5-azido-2,3,4,6-tCtra-0-benzyl-5-dCsoxy-et 2,3,4,6-tttra-0-benzyl-5-dCsoxy-5-trifluoroacCtamido-D-glucononitriles ?I partir du D-glucose. On a essay6 sans succks de transformer ces deux compos6s en un ~-amino-5-d6soxy-~-glucononitrile et Cventuellement de les cycliser en une amidine analogue du glucose qui aurait pu &tre tvaluCe cornrne inhibiteur de la glycosidase.Mots cle's : synthkse, amino-sucres, inhibiteurs de la glycosidase.[Traduit par la revue]

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Section: Resultsmentioning

confidence: 99%

The synthesis of protected 5-azido-5-deoxy-D-glucononitriles as precursors of glycosidase inhibitors

Bird¹,

Dolphin²,

Withers³

1990

Can. J. Chem.

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“…[19] This diverse biological activity of anisomycin has stimulated many scientists to develop new routes for its synthesis, both in racemic and in enantiopure form. [20] Retrosynthetically, anisomycin could be prepared from the 3,4-dehydropyrrolidine 28, as described by Jegham and Das. [19d,k] To produce 28 from a starting propargylic amine would afford a formal synthesis of (+)-anisomycin (29 b) now based on the enantioselective copper-catalysed propargylic amination.…”

Section: Applicationsmentioning

confidence: 99%

Enantioselective Copper‐Catalysed Propargylic Substitution: Synthetic Scope Study and Application in Formal Total Syntheses of (+)‐Anisomycin and (−)‐Cytoxazone

Detz¹,

Abiri²,

Griel³

et al. 2011

Chemistry A European J

123

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A copper catalyst with a chiral pyridine-2,6-bisoxazoline (pybox) ligand was used to convert a variety of propargylic esters with different side chains (R=Ar, Bn, alkyl) into their amine counterparts in very high yields and with good enantioselectivities (up to 90% enantiomeric excess (ee)). Different amine nucleophiles were applied in the reactions and the highest enantioselectivities were obtained for aniline and its analogues. Interestingly, some carbon nucleophiles could also be used and with indoles excellent ee values were obtained (up to 98% ee). The versatility of the propargylic amines obtained was demonstrated by their further elaboration to formal total syntheses of the antibiotic (+)-anisomycin and the cytokine modulator (-)-cytoxazone.

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“…No. 638 [3] and Streptomyces SA 3097 [4]. Anisomycin has a broad activity against certain pathogenic protozoa, strains of fungi [1][2][3][4][5][6][7][8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

“…It has high antitumor activity in vitro, with IC 50 values in the nanomolar range [3,4]. Anisomycin may be used in a synergistic fashion with a cyclindependent protein kinase inhibitor to kill carcinoma cells [19][20][21].…”

Section: Introductionmentioning

confidence: 99%