Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)-tetrahydrofuran-2-carboxylic acid

Uhrig, Marı́a Laura; Simirgiotis, Mario J.; Varela, Oscar

doi:10.1016/j.tetasy.2010.08.013

Cited by 4 publications

(3 citation statements)

References 36 publications

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“…S7, supporting information), which are in coincidence with the HMBC and NOESY spectra for compound 3 ( Table 1 and Table 2) and with the structure proposed. Compound 4 was subjected to alkaline hydrolysis with potassium carbonate in methanol 35,36 yielding 3 in 91% yield (see experimental) which confirmed 3 as the deacetyl derivative of 4. Compound 3 was oxidized with pyridinium chlorochromate in CHCl 3 at room temperature to give compound 2 in 70.5% yield.…”

Section: Structural Elucidation Of the New Diterpenoidsmentioning

confidence: 82%

“…Compound 4 (5 mg, 0.014 mmol) was dissolved in MeOH (5 mL), 5 mg of K 2 CO 3 was added and the mixture stirred at room temperature for 2 h. Afterwards the reaction mixture was neutralized with Dowex 50 W (H + ), filtered and concentrated . The residue was subjected to normal phase silica gel flash chromatography using n ‐hexane/EtOAc 9:1 to yield 4 mg (0.013 mmol) of compound 3 (91% yield).…”

Section: Methodsmentioning

confidence: 99%

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Isolation of cytotoxic diterpenoids from the Chilean medicinal plantAzorella compactaPhil from the Atacama Desert by high-speed counter-current chromatography

Bórquez

Bartolucci²,

Echiburú-Chau

et al. 2015

J. Sci. Food Agric.

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Section: Structural Elucidation Of the New Diterpenoidsmentioning

confidence: 82%

Section: Methodsmentioning

confidence: 99%

Isolation of cytotoxic diterpenoids from the Chilean medicinal plantAzorella compactaPhil from the Atacama Desert by high-speed counter-current chromatography

Bórquez

Bartolucci²,

Echiburú-Chau

et al. 2015

J. Sci. Food Agric.

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show abstract

“…Mario Simirgiotis has worked previously on the synthesis of small molecules starting from sugars as chiral templates [26] and embarked on the synthesis of this compound several years ago (under the mentorship of Dr. Oscar Varela, at the University of Buenos Aires, Argentina), but the results were unpublished.…”

Section: Introductionmentioning

confidence: 99%

Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid

et al. 2014

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An enantioselective total synthesis of the natural amino acid (2S,4R,5R)-4,5-dihydroxy-pipecolic acid starting from D-glucoheptono-1, 4-lactone is presented. The best sequence employed as a key step the intramolecular nucleophilic displacement by an amino function of a 6-O-p-toluene-sulphonyl derivative of a methyl D-arabino-hexonate and involved only 12 steps with an overall yield of 19%. The structures of the compounds synthesized were elucidated on the basis of comprehensive spectroscopic (NMR and MS) and computational analysis.

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A compendium of cyclic sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues

et al. 2013

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This compendium focuses on functionalised sugar amino acids (SAAs) and their 3- to 6-membered nitrogen heterocyclic and carbocyclic analogues. The main benefit of using SAAs and their related nitrogen and carbon congeners in the production of peptidomimetics and glycomimetics is that their properties can be readily altered via modification of their ring size, chemical manipulation of their numerous functional groups and fine-tuning of the stereochemical arrangement of their ring substituents. These building blocks provide access to hydrophilic and hydrophobic peptide isosteres whose physical properties allow entry to a region of chemotherapeutic space which is still under-explored by medicinal chemists. These building blocks are also important in providing amino acids whose inherent conformational bias leads to predisposition to secondary structure upon oligomerisation in relatively short sequences. These foldamers, particularly those containing ω-amino acids, provide an additional opportunity to expand access to the control of structures by artificial peptides. The synthesis and biological evaluation of these building blocks in glycomimetics and peptidomimetics systems keep expanding the reach of the glycosciences to the medical sciences, provide a greater outlook onto the wide range of cellular functions of saccharides and their derivatives involved and greater insight into the nature of oligosaccharide and protein folding.

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Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)-tetrahydrofuran-2-carboxylic acid

Cited by 4 publications

References 36 publications

Isolation of cytotoxic diterpenoids from the Chilean medicinal plantAzorella compactaPhil from the Atacama Desert by high-speed counter-current chromatography

Isolation of cytotoxic diterpenoids from the Chilean medicinal plantAzorella compactaPhil from the Atacama Desert by high-speed counter-current chromatography

Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid

A compendium of cyclic sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues

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