Stereodivergent synthesis of threo and erythro 6-amino-6-deoxyheptosulose derivatives via an optically active oxazolidine aldehyde

Garner, Philip; Sarabu, Ramakanth

doi:10.1021/jo00363a044

Cited by 99 publications

(37 citation statements)

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“…We first attempted to use the Wittig reaction with several combinations of the intermediates (eg. Garners aldehyde [39] and the corresponding bromide), but most of these reactions yielded an epimeric mixture of the compounds. We then used Kocienski-modified Julia olefination (Scheme 1), [40] utilizing an aldehyde 9 [41] and a sulfone 10, [42] both of which were derived from d-serine.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Diaminopimelic Acid Containing Peptidoglycan Fragments and Tracheal Cytotoxin (TCT) and Investigation of Their Biological Functions

Kawasaki

Karasudani

Otsuka

et al. 2008

Chemistry A European J

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Bacterial cell wall peptidoglycan (PGN) is a potent immunostimulator and immune adjuvant. The PGN of Gram-negative bacteria and some Gram-positive bacteria contain meso-diaminopimelic acid (meso-DAP), and we have recently shown that the intracellular protein Nod1 is a PGN receptor and recognizes DAP-containing peptides. In this study, we achieved the synthesis of DAP-containing PGN fragments, including the first chemical synthesis of tracheal cytotoxin (TCT), GlcNAc-(beta1-4)-(anhydro)MurNAc-L-Ala-gamma-D-Glu-meso-DAP-D-Ala, and a repeating-unit of DAP-type PGN, GlcNAc-(beta1-4)-MurNAc-L-Ala-gamma-D-Glu-meso-DAP-D-Ala. For the synthesis of PGN fragments, we first established a new synthetic method for an orthogonally protected meso-DAP derivative, and then we constructed the glycopeptide structures. The ability of these fragments to stimulate human Nod1, as well as differences in Nod1 recognition of the variety of synthesized ligand structures were examined. The results showed that the substitution of the N terminus of iE-DAP is necessary for stronger Nod1 recognition, but the structure of the substituent seems not to be strictly recognized. The importance of the carboxyl group at the 2-position of DAP for human Nod1 stimulation was also shown.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Diaminopimelic Acid Containing Peptidoglycan Fragments and Tracheal Cytotoxin (TCT) and Investigation of Their Biological Functions

Kawasaki

Karasudani

Otsuka

et al. 2008

Chemistry A European J

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“…Many syntheses of sphingosine and its analogues18192021 are based on serine or Garner aldehyde2223242526. This chiral building block not only provides the C-2 stereocenter, but enables the introduction of the C-3 stereocenter upon addition of terminal alkynes to form fragment sphingosine222324252627.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Chrysogeside B from Halotolerant Fungus Penicillium and Its Antimicrobial Activities Evaluation

Liu

Wang²,

et al. 2017

Sci Rep

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Chrysogeside B, a natural cerebroside, was efficiently synthesized from commercial feedstocks. The bioassays showed that compounds 4, 5 and 6 exhibited enhanced biological activities compared Chrysogeside B. Further studies revealed that free hydroxyl groups and glycosidic bond have significant impact on the antimicrobial activities. The synthesis of Chrysogeside B and analogues designed to allow identification of the features of this glycolipid required for recognition by tested bacteria and Hela cells is described.

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“…Based on these results, and taking into account the well-documented use of Garner's aldehyde in similar stereocontrolled HDA cycloadditions, 9,11,12 we decided to investigate the suitability of oxazolidine 6 instead of acetonide 3 as the dienophile in the BF 3 -catalyzed reaction. This route would lead to a precursor of the C3-C17 fragment bearing an oxazolidine ring on C-15, which, as we have recently shown, 7 can be readily converted into the oxazole moiety present in the parent compound.…”

Section: Resultsmentioning

confidence: 99%

“…6,7 Herein we report a high-yielding and stereoselective route for the preparation of key intermediates in the synthesis of analogues of the C3-C17 oxazole oxane fragment of these molecules (Scheme 1). The approach relies on the BF 3 -catalyzed hetero Diels-Alder (HDA) reaction between Danishefsky's diene and Garner's aldehyde, 8,9 and leads to a trans-2,6-disubstituted tetrahydropyranone as the major product. Particular emphasis is made on the determination of the stereochemistry of the products, which was achieved via a combination of spectroscopic and computational studies on the reaction products and rigid derivatives.…”

Section: Introductionmentioning

confidence: 99%

Insights into the stereoselective BF3-catalyzed hetero Diels–Alder reaction of Garner’s aldehyde with Danishefsky’s diene

Fontana

Incerti

Moyna

et al. 2010

Tetrahedron: Asymmetry

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Stereodivergent synthesis of threo and erythro 6-amino-6-deoxyheptosulose derivatives via an optically active oxazolidine aldehyde

Cited by 99 publications

References 0 publications

Synthesis of Diaminopimelic Acid Containing Peptidoglycan Fragments and Tracheal Cytotoxin (TCT) and Investigation of Their Biological Functions

Synthesis of Diaminopimelic Acid Containing Peptidoglycan Fragments and Tracheal Cytotoxin (TCT) and Investigation of Their Biological Functions

Synthesis of Chrysogeside B from Halotolerant Fungus Penicillium and Its Antimicrobial Activities Evaluation

Insights into the stereoselective BF3-catalyzed hetero Diels–Alder reaction of Garner’s aldehyde with Danishefsky’s diene

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