Synthesis of Aminocyclitols and Trihydroxylated Indolizidinone from a <scp>D</scp>‐Mannitol‐Derived Common Building Block

Gupta, Preeti; Pal, A. P. John; Reddy, Y. Suman; Vankar, Yashwànt D.

doi:10.1002/ejoc.201001171

Cited by 27 publications

(4 citation statements)

References 54 publications

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“…The 2S,3R,4R,5R configuration was confirmed quite recently, through NMR techniques, in a refined synthesis protocol starting from D-mannitol. 42 The RCM-derived synthon (70), stepwise constructed from the azide 67, acts as a pivotal intermediate prone to provide access to a variety of mono-and bicyclic azasugars (e.g. trihydroxylated indolizidinone), through suitable functionalisation of the double bond and manipulation of the protecting groups (Scheme 17).…”

Section: -Deoxynojirimycin and Analoguesmentioning

confidence: 99%

Targeted drugs by olefin metathesis: piperidine-based iminosugars

Drăguţan

Demonceau

2012

RSC Adv.

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Section: -Deoxynojirimycin and Analoguesmentioning

confidence: 99%

Targeted drugs by olefin metathesis: piperidine-based iminosugars

Drăguţan

Demonceau

2012

RSC Adv.

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“…Valienamine (3) and its analogues show inhibitory activity against certain glycosidases [11][12][13] (Figure 1). Many groups have described different synthetic methods for the synthesis of various aminocyclitols [13][14][15][16][17]. However, only few synthetic methods are available for the synthesis of eight-membered [18][19][20][21][22][23][24][25][26][27][28][29] aminocyclitols.…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

Salamci¹,

Lafzi²

2022

Beilstein J. Org. Chem.

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Cyclooctene endoperoxide was used as the key compound for the synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol. Reduction of the cyclooctene endoperoxide, prepared by photooxygenation of cis,cis-1,3-cyclooctadiene, with zinc gave a cyclooctenediol and then benzylation of the hydroxy group yielded dibenzylated cyclooctene. Oxidation of the latter compound by OsO4/NMO followed by mesylation of the hydroxy group provided bis(benzyloxy)cyclooctane-1,2-diyl dimethanesulfonate. Reaction of the bis(benzyloxy)cyclooctane-1,2-diyl dimethanesulfonate with NaN3 gave 2-azido-3,8-bis(benzyloxy)cyclooctyl methanesulfonate. Reduction of the azide group and debenzylation to give an amine provided the new 3-aminocyclooctanetriol. Treatment of the 2-azido-3,8-bis(benzyloxy)cyclooctyl methanesulfonate with Zn/NH4Cl and debenzylation resulted in the target aziridinecyclooctanediol.

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“…Glycosidase inhibitors are known to be antidiabetic, anti‐influenza, antimicrobial, herbicidal, antitumor, antibacterial, [13a] antileukemia, anti‐HIV, and antihypergens, and they are also responsible for intercellular recognition, signal transduction, and cellular development …”

Section: Introductionmentioning

confidence: 99%

rac‐ and meso‐Cyclohexanoids: Their α‐, β‐glycosidases, antibacterial, antifungal activities, and molecular docking studies

Karakılıç

Baran

Öğütçü

et al. 2020

Archiv der Pharmazie

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An efficient and versatile synthesis method has been postulated for hydroxymethylated rac‐ and meso‐cyclohexanoid derivatives. The synthesis of these stereoisomers was achieved easily with traditional methods using hexahydroisobenzofuran 6, prepared from commercially available cis‐hydrophthalic anhydride. The study, involving diastereoselective epoxidation and cis‐hydroxylation, was conducted to obtain epoxy‐, cis‐, and trans‐diol‐furans 7, 8, and 9. After sulfamic acid‐catalyzed ring‐opening reaction of the epoxide and furan rings, rac‐ and meso‐tetraacetates 14, 15, and 16 were afforded. Hydrolysis of acetate groups with ammonia in absolute methanol yielded the desired tetrols rac‐17, meso‐18, and meso‐19. All structures, after purification by chromatographic methods and elucidation by spectral techniques, were screened against α‐ and β‐glucosidases. Compounds 7, 8, 10, 17, 18, and 19 were also evaluated for their antibacterial and antifungal activity against some selected synthesized compounds with varying degrees of inhibitory effects on the growth of different pathogenic microorganisms by the well‐diffusion method. In addition, Saccharomyces cerevisiae α‐glucosidase molecular modeling studies were performed for all rac‐ and meso‐compounds 7, 8, 10, 17, 18, and 19.

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Synthesis of Aminocyclitols and Trihydroxylated Indolizidinone from a D‐Mannitol‐Derived Common Building Block

Abstract: The synthesis of 4‐amino‐4‐deoxy‐muco‐quercitol (22), 4‐amino‐4‐deoxy‐(–)‐vibo‐quercitol (27) and also a trihydroxylated indolizidinone 38 from D‐mannitol is described using ring‐closing metathesis and diastereoselective dihydroxylation as the key steps.

Cited by 27 publications

References 54 publications

Targeted drugs by olefin metathesis: piperidine-based iminosugars

Targeted drugs by olefin metathesis: piperidine-based iminosugars

Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

rac‐ and meso‐Cyclohexanoids: Their α‐, β‐glycosidases, antibacterial, antifungal activities, and molecular docking studies

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