Metathesis and Macrocycles with Embedded Carbohydrates

Jarikote, Dilip V.; Murphy, Paul V.

doi:10.1002/ejoc.201000491

Cited by 35 publications

(19 citation statements)

References 109 publications

(39 reference statements)

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“…Because of their unique macrocyclic architectures with embedded carbohydrates and a broad spectrum of biological activities, resin glycosides have attracted considerable attention from the synthetic community, but not much beyond. 3–5 …”

Section: Introductionmentioning

confidence: 99%

Total Synthesis and Biological Evaluation of Ipomoeassin F and Its Unnatural 11R-Epimer

et al. 2015

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Ipomoeassin F, a macrolide glycoresin containing an embedded disaccharide, possesses potent in vitro antitumor activity with an unknown mechanism of function. It inhibits tumor cell growth with single-digit nanomolar IC50 values, superior to many clinical chemotherapeutic drugs. To facilitate translation of its bioactivity into protein function for drug development, we report here a new synthesis for the gram-scale production of ipomoeassin F (3.8% over 17 linear steps) from commercially-available starting materials. The conformation-controlled subtle reactivity differences of the hydroxyl groups in carbohydrates were utilized to quickly construct the disaccharide core, which, along with judicial selection of protecting groups, made the current synthesis very efficient. The same strategy was also applied to the smooth preparation of the 11R-epimer of ipomoeassin F for the first time. Cytotoxicity assays demonstrated the crucial role of the natural 11S configuration. In addition, cell cycle analyses and apoptosis assays on ipomoeassin F and/or its epimer were conducted. This work has laid a solid ground for understanding the medicinal potential of the ipomoeassin family of glycolipids in the future.

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Section: Introductionmentioning

confidence: 99%

Total Synthesis and Biological Evaluation of Ipomoeassin F and Its Unnatural 11R-Epimer

et al. 2015

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“…To mimic the natural disaccharidic substrates, the two units were linked by a short and flexible alkyl bridge; the Grubbs Ru-carbene-catalyzed CM reaction [13] was used to connect the two moieties suitably functionalized with a double bond, as outlined in the retrosynthetic scheme (Scheme 1). Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Iminosugar‐Based Trehalase Inhibitors by Cross‐Metathesis Reactions

et al. 2011

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The synthesis of a novel class of trehalase inhibitors composed of iminopyranose or iminofuranose residues linked at the pseudoanomeric carbon through an alkyl chain is described. A set of six novel compounds was prepared by the same reaction sequence involving the Grubbs Ru–carbene‐catalyzed cross‐metathesis (CM) of different N‐Cbz‐protected allyl C‐iminoglycosides as the key step in homo‐ or heterodimerization reactions. The target products, obtained with the CM reaction, were fully hydrogenated by catalytic hydrogenolysis, and preliminary biological screening of the products as inhibitors of commercially available porcine trehalase was performed.

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“…[132][133][134][135] These synthetic receptors served as model systems for studying carbohydrate-carbohydrate interactions in water. 137 (235) 138,139 was converted into the α-D-glucopyranosiduronic acid derivatives 237 by highly selective glycosidation reaction with the triethylsilane ethers 236. 137 (235) 138,139 was converted into the α-D-glucopyranosiduronic acid derivatives 237 by highly selective glycosidation reaction with the triethylsilane ethers 236.…”

Section: Nitrogen-containing Glycophanesmentioning

confidence: 99%