Synthesis of α,ω-polyfluorinated α-amino acid derivatives and δ,δ-difluoronorvaline

Ulbrich, Dirk; Daniliuc, Constantin G.; Haufe, Günter

doi:10.1039/c6ob00131a

Cited by 12 publications

(4 citation statements)

References 51 publications

(78 reference statements)

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“…According to the literature, [12] N-bromosuccinimide (NBS) has frequently been used as a brominating agent for phenyl rings. [15] When pyridinium 4-toluenesulfonate (PPTS) was added, the isolated yield of dibromide 7 improved to 86 % (Table 1, entry 6). When the reaction mixture was heated at reflux for 8 h, only a trace amount of the target dibromide 7 was identified ( Table 1, entry 2).…”

Section: Resultsmentioning

confidence: 99%

First Total Syntheses of Amorfrutin C and pseudo‐Amorfrutin A

Miao

et al. 2018

Eur J Org Chem

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Syntheses of amorfrutin C, a natural product with potent antitumor activity, as well as pseudo‐amorfrutin A were accomplished. Protected 2,4‐dihydroxybenzoic acid derivative 5 was used as a common synthetic intermediate. The introduction of a prenyl moiety to 5 was achieved through bromination followed by a CuCN‐meditated alkylation reaction. Interestingly, N‐bromosuccinimide promoted monobromination at the 6‐position, leading to pseudo‐amorfrutin A; 1,3‐dibromo‐5,5‐dimethylhydantoin triggered bromination at both the 6‐ and 8‐positions, leading to naturally occurring amorfrutin C.

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Section: Resultsmentioning

confidence: 99%

First Total Syntheses of Amorfrutin C and pseudo‐Amorfrutin A

Miao

et al. 2018

Eur J Org Chem

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“…Hydrogenation of the benzyl group of 107 and oxidation of the resulting primary hydroxy group with DMP gave the corresponding aldehyde which was then treated with Deoxo-Fluor giving N -Phth-5,5-difluoronorvaline derivative 108 as the major product (Scheme ). During the fluorination reaction, the authors also observed an occurring cyclization reaction …”

Section: Fluorinated Alkyl α-Amino Acidsmentioning

confidence: 99%

“…During the fluorination reaction, the authors also observed an occurring cyclization reaction. 104 3.5.3. Methyl 2-((Boc)Amino-5,5,5-trifluoropentanoate (5,5,.…”

Section: T H Imentioning

confidence: 99%

Approaches to Obtaining Fluorinated α-Amino Acids

et al. 2019

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Fluorine does not belong to the pool of chemical elements that nature uses to build organic matter. However, chemists have exploited the unique properties of fluorine and produced countless fluoro-organic compounds without which our everyday lives would be unimaginable. The incorporation of fluorine into amino acids established a completely new class of amino acids and their properties, and those of the biopolymers constructed from them are extremely interesting. Increasing interest in this class of amino acids caused the demand for robust and stereoselective synthetic protocols that enable straightforward access to these building blocks. Herein, we present a comprehensive account of the literature in this field going back to 1995. We place special emphasis on a particular fluorination strategy. The four main sections describe fluorinated versions of alkyl, cyclic, aromatic amino acids, and also nickel-complexes to access them. We progress by one carbon unit increments. Special cases of amino acids for which there is no natural counterpart are described at the end of each section. Synthetic access to each of the amino acids is summarized in form of a table at the end of this article with the aim to make the information easily accessible to the reader.

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“…Acyclic non-aromatic motifs are the most prevalent in naturally occurring amino acids. Therefore, the ability to access either fluorinated analogues or completely novel acyclic motifs is of utmost importance for applications such as biological probes and peptide therapeutics [ [133] , [134] , [135] , [136] , [137] , [138] , [139] ]. There have been many reports of the synthesis of singly fluorinated analogues of naturally occurring acyclic amino acids [ 12 ].…”

Section: Complex Fluorine-containing Non-aromatic Amino Acidsmentioning

confidence: 99%