Synthesis of γ‐Aminobutyric Acid Analogs

Hanrahan, Jane R.; Johnston, Graham A.R.

doi:10.1002/9783527631766.ch14

Cited by 5 publications

(4 citation statements)

References 395 publications

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“…Remarkably, these reactions enabled the one-step construction of the neurotransmitter g-aminobutyric acid (GABA) in a protected form (3 aa) as well as of its a-or bfunctionalized artificial analogues 3 ab-af. [18] The synthetic generality of the decarbonylative CÀC bond formation was further corroborated by applying 1 b-k as the radical donors and methyl acrylate 2 a as a radical acceptor (Scheme 3). The corresponding primary a-amino carbon radicals from glutamic acid derived 1 b and dihydroxyphenylalanine-derived 1 c were efficiently formed in the presence of 3 SiH, and air, leading to 3 b and 3 c, respectively, after their addition to 2 a.…”

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confidence: 91%

“…Previous and present methods for the generation of a-amino carbon radicals, and possible reaction mechanism of the decarbonylative radical coupling. [18] The synthetic generality of the decarbonylative CÀC bond formation was further corroborated by applying 1 b-k as the radical donors and methyl acrylate 2 a as a radical acceptor (Scheme 3). [14] Eleven structurally distinct a-aminoacyl tellurides 1 a-k were prepared from readily available N-Boc-protected a-amino acids 6 a-k in a single step (Scheme 2).…”

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confidence: 98%

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Decarbonylative Radical Coupling of α‐Aminoacyl Tellurides: Single‐Step Preparation of γ‐Amino and α,β‐Diamino Acids and Rapid Synthesis of Gabapentin and Manzacidin A

et al. 2014

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A new radical-based coupling method has been developed for the single-step generation of various γ-amino acids and α,β-diamino acids from α-aminoacyl tellurides. Upon activation by Et3 B and O2 at ambient temperature, α-aminoacyl tellurides were readily converted into α-amino carbon radicals through facile decarbonylation, which then reacted intermolecularly with acrylates or glyoxylic oxime ethers. This mild and powerful method was effectively incorporated into expeditious synthetic routes to the pharmaceutical agent gabapentin and the natural product (-)-manzacidin A.

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confidence: 91%

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confidence: 98%

Decarbonylative Radical Coupling of α‐Aminoacyl Tellurides: Single‐Step Preparation of γ‐Amino and α,β‐Diamino Acids and Rapid Synthesis of Gabapentin and Manzacidin A

et al. 2014

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mentioning

confidence: 91%

Decarbonylative Radical Coupling of α‐Aminoacyl Tellurides: Single‐Step Preparation of γ‐Amino and α,β‐Diamino Acids and Rapid Synthesis of Gabapentin and Manzacidin A

et al. 2014

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A new radical-based coupling method has been developed for the single-step generation of various g-amino acids and a,b-diamino acids from a-aminoacyl tellurides. Upon activation by Et 3 B and O 2 at ambient temperature, a-aminoacyl tellurides were readily converted into a-amino carbon radicals through facile decarbonylation, which then reacted intermolecularly with acrylates or glyoxylic oxime ethers. This mild and powerful method was effectively incorporated into expeditious synthetic routes to the pharmaceutical agent gabapentin and the natural product (À)-manzacidin A.

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“…Although many highly substituted derivatives of cyclic aamino acids 26 or cyclic g-amino acids 27,28 with biological properties have been synthesized and investigated, the functionalized b-amino acids have received appreciably less attention. The most relevant examples of highly functionalized cyclic g-amino acids are probably the antiviral agents zanamivir [29][30][31] and oseltamivir (tamiflu, 4).…”

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confidence: 99%

Selective Syntheses of Functionalized Cyclic β-Amino Acids via Transformation of the Ring C-C Double Bonds

Kiss¹,

Fülöp²

2010

Synlett

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This report provides an overview of the most important aspects of the syntheses of functionalized cyclic b-amino acids in recent years. The presentation focuses in particular on strategies involving the selective functionalization of unsaturated alicyclic bamino acids. The limitations and shortcomings of the synthetic methods are emphasized, and the possible new challenges and developments in this field in the near future are outlined. Double Bonds 3 Some Relevant Routes to Functionalized Cyclic b-Amino Acids other than Functionalization of Ring C-C Double Bonds 4 Conclusions

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Synthesis of γ‐Aminobutyric Acid Analogs

Cited by 5 publications

References 395 publications

Decarbonylative Radical Coupling of α‐Aminoacyl Tellurides: Single‐Step Preparation of γ‐Amino and α,β‐Diamino Acids and Rapid Synthesis of Gabapentin and Manzacidin A

Decarbonylative Radical Coupling of α‐Aminoacyl Tellurides: Single‐Step Preparation of γ‐Amino and α,β‐Diamino Acids and Rapid Synthesis of Gabapentin and Manzacidin A

Decarbonylative Radical Coupling of α‐Aminoacyl Tellurides: Single‐Step Preparation of γ‐Amino and α,β‐Diamino Acids and Rapid Synthesis of Gabapentin and Manzacidin A

Selective Syntheses of Functionalized Cyclic β-Amino Acids via Transformation of the Ring C-C Double Bonds

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