Iminoiodane mediated aziridination of α-allylglycine: access to a novel rigid arginine derivative and to the natural amino acid enduracididine

Sanière, Laurent; Leman, Loïc; Bourguignon, Jean‐Jacques; Dauban, Philippe; Dodd, Robert H.

doi:10.1016/j.tet.2004.05.034

Cited by 42 publications

(41 citation statements)

References 39 publications

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“…67 The key step was the aziridination of the suitably protected allylglycine derivatives 88 (Scheme 40). Not surprisingly, the nitrogen protecting-group appeared to have an influence on the course of the reaction.…”

Section: Copper-catalyzed Nitrogen Atom Transfermentioning

confidence: 99%

Iminoiodanes and C-NBond Formation in Organic Synthesis

Dauban¹,

Dodd²

2003

Synlett

Self Cite

281

129

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Structurally related to iodosylbenzene PhI=O, iodonium imides PhI=NR, off-white to pale yellow solids of low solubility, belong to the class of hypervalent iodine(III) reagents and were first prepared nearly thirty years ago. Two additional decades were needed before they could be considered as useful nitrene precursors with the discovery of the copper-catalyzed aziridination of olefins. Since then, iminoiodanes have been successfully applied in the total synthesis of natural and/or biologically active compounds. Recent developments aimed at circumventing their tedious preparation led to the discovery of one-pot nitrogen transfers from sulfonamides, sulfamates, or carbamates mediated by iodosylbenzene(diacetate) PhI(OAc) 2 or iodosylbenzene. Reliable functionalizations of alkanes and alkenes via C-H insertion or aziridination using copper or rhodium catalysts can now be considered as synthetically useful processes.

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Section: Copper-catalyzed Nitrogen Atom Transfermentioning

confidence: 99%

Iminoiodanes and C-NBond Formation in Organic Synthesis

Dauban¹,

Dodd²

2003

Synlett

Self Cite

281

129

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“…Synthesis of enduracididine and allo-enduracididine by Dodd et al: No further synthetic investigations were reported until 2004 when Dodd et al published a synthesis of protected enduracididine using an azide ring opening of a chiral aziridine as the key step (Scheme 3) [55]. The 9-phenylfluorenyl (PhF) protecting group was employed to help prevent undesired copper coordination during the key aziridation step.…”

Section: Reviewmentioning

confidence: 99%

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

Atkinson¹,

Naysmith²,

Furkert³

et al. 2016

Beilstein J. Org. Chem.

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Rising resistance to current clinical antibacterial agents is an imminent threat to global public health and highlights the demand for new lead compounds for drug discovery. One such potential lead compound, the peptide antibiotic teixobactin, was recently isolated from an uncultured bacterial source, and demonstrates remarkably high potency against a wide range of resistant pathogens without apparent development of resistance. A rare amino acid residue component of teixobactin, enduracididine, is only known to occur in a small number of natural products that also possess promising antibiotic activity. This review highlights the presence of enduracididine in natural products, its biosynthesis together with a review of analogues of enduracididine. Reported synthetic approaches to the cyclic guanidine structure of enduracididine are discussed, illustrating the challenges encountered to date in the development of efficient synthetic routes to facilitate drug discovery efforts inspired by the discovery of teixobactin.

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“…The remaining hurdle to the total synthesis of the natural product is then the availability of the unusual amino acid l ‐ allo ‐enduracididine. The presence of enduracididine in several prominent peptides has inspired efforts to devise its synthesis from simple precursors . Achieving the correct chirality at C4 is the primary difficulty in synthesising this amino acid .…”

Section: Lipid II Inhibitors As Therapeutic Agentsmentioning

confidence: 99%

“…Other research groups undertook alternative methods of synthesising the amino acid from commercially available allylglycine, namely, one‐pot iminoiodane‐mediated tandem aziridation and ring‐opening reactions, as well as the Rh‐catalysed approach. However, neither diasteroselectivity nor yield was satisfactory . The situation may have been turned around as Craig et al.…”

Section: Lipid II Inhibitors As Therapeutic Agentsmentioning

confidence: 99%

New Found Hope for Antibiotic Discovery: Lipid II Inhibitors

Chan

2016

Chemistry A European J

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Abstract:Research into antibacterial agents has recently gathered pace in light of the disturbing crisis of antimicrobial resistance. Development of modern tools offers opportunity of reviving the fallen era of antibacterial discovery through uncovering novel lead compounds that target vital bacterial cell components, such as lipid II. This paper provides a summary of the role of lipid II as well as an overview and insight into the structural features of macrocyclic peptides that inhibit this bacterial cell wall component. The recent discovery of teixobactin, a new class of lipid II inhibitor has generated substantial research interests. As such, the significant progress that has been achieved towards its development as a promising antibacterial agent is discussed.

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Iminoiodane mediated aziridination of α-allylglycine: access to a novel rigid arginine derivative and to the natural amino acid enduracididine

Cited by 42 publications

References 39 publications

Iminoiodanes and C-NBond Formation in Organic Synthesis

Iminoiodanes and C-NBond Formation in Organic Synthesis

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

New Found Hope for Antibiotic Discovery: Lipid II Inhibitors

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