Synthesis of (2<i>S</i>)-2-Chloro-2-fluororibolactone via Stereoselective Electrophilic Fluorination

Schutter, Coralie De; Sari, Ozkan; Coats, Steven J.; Amblard, Franck; Schinazi, Raymond F.

doi:10.1021/acs.joc.7b02245

Cited by 8 publications

(9 citation statements)

References 43 publications

(72 reference statements)

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“…Synthetically developed and natural ribolactones derivatives are included as building blocks of several antiviral regimens [34]. The diversity and availability of these relatively cheap chiral compounds has led to their use as starting materials for the design and syntheses of naturally occurring compounds and biologically important molecules [35, 36].…”

Section: Resultsmentioning

confidence: 99%

Bioactive secondary metabolites from new endophytic fungus Curvularia. sp isolated from Rauwolfia macrophylla

et al. 2019

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Over the last decades, endophytic fungi represent a new source of pharmacologically active secondary metabolites based on the underlying assumption that they live symbiotically within their plant host. In the present study, a new endophytic fungus was isolated from Rauwolfia macrophylla , a medicinal plant from Cameroon. The fungus showed a highest homology to Curvularia sp. based on complete nucleotide sequence data generated from the internal transcribed spacer (ITS) of ribosomal DNA region. Large scale fermentation, working-up and separation of the strain extract using different chromatographic techniques afforded three bioactive compounds: 2'-deoxyribolactone ( 1 ), hexylitaconic acid ( 2 ) and ergosterol ( 3 ). The chemical structures of compounds 1–3 were confirmed by 1 and 2D NMR spectroscopy and mass spectrometry, and comparison with corresponding literature data. Biologically, the antimicrobial, antioxidant activities and the acetylcholinesterase inhibitory of the isolated compounds were studied.

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Section: Resultsmentioning

confidence: 99%

Bioactive secondary metabolites from new endophytic fungus Curvularia. sp isolated from Rauwolfia macrophylla

et al. 2019

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“…Subsequent diastereoselective introduction of fluorine was accomplished using lithium bis(trimethylsilyl)amide and N -fluorobenzenesulfonimide as a source of fluorine. It is worth noting that 25 and 30 were obtained as single isomers and that unlike what was observed with previous methods, , no β-elimination of tert -butyldimethylsiloxide occurred during the fluorination reaction. Finally, the key dihaloribolactones 26 and 40 were readily obtained by cyclization in the presence of acetic acid in water/acetonitrile at reflux, followed by 5- tert -butyldimethylsilyl protection with tert -butyldimethylsilyl chloride in dimethylformamide .…”

Section: Resultsmentioning

confidence: 99%

“…Herein, we wish to report the optimization and extension of our recently published approach for the preparation of (2 S )-2-chloro-2-fluoro ribolactone 26 via pivotal aldol and diastereoselective fluorination reactions ( Scheme 1 ). 12 …”

Section: Introductionmentioning

confidence: 99%

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Diastereoselective Synthesis of 2′-Dihalopyrimidine Ribonucleoside Inhibitors of Hepatitis C Virus Replication

Zhou

Zhang

et al. 2021

ACS Omega

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We present a newly developed synthetic route to 2-bromo-2-fluoro ribolactone based on our published 2-chloro-2-fluoro ribolactone synthesis. Stereoselective fluorination is key to controlling the 2-diastereoselectivity. We also report a substantially improved glycosylation reaction with both the 2-bromo-2-fluoro and 2-chloro-2-fluoro sugars. These improvements allowed us to prepare 2′-dihalo nucleosides 13 and 14 in an overall 15–20% yield.

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“…In 2017, Schinazi and his co‐workers, developed a novel and efficient route for the preparation of (2 S )‐2‐chloro‐2‐fluorolactone 243 , which was used as a potent non‐toxic pangenotypic anti‐HCV agent (Scheme B). The gem ‐dihaloketone precursor 244 was employed as the key precursor to obtain the product in an extra 30 % overall yield in comparison to the original four‐step synthesis .…”

Section: The Gem‐dihaloketones In the Synthesis Of Heterocyclic Framementioning

confidence: 99%

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

Sadhukhan

Santhi

Baire

2020

Chemistry A European J

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The α,α‐dihalocarbonyl moiety is a bifunctional system with a gem‐dihalocarbon and a carbonyl carbon in 1,2‐fashion. This is one of the privileged scaffolds in medicinal chemistry due to its chemical and metabolic stability and lipophilicity. They have also been found in numerous structurally divergent natural products and most of their fabricated structures have already been in medicinal use. Apart from their important use in medicinal chemistry, the α,α‐dihalocarbonyl groups have been employed as key building blocks for the development of novel synthetic strategies and utilized as intermediates in total synthesis. In addition to the traditional transformations such as oxidations, reductions, and C−C bond formations, recently several new and non‐classical reactions have also been developed. This review provides short description of existing methods for their synthesis and detailed discussion on the efforts for the discovery and development of new reactions by employing α,α‐dihaloketones as synthetic building blocks. We have presented their use as key functional groups for the synthesis of polycyclic systems of medicinal and material importance and natural products.

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Synthesis of (2S)-2-Chloro-2-fluororibolactone via Stereoselective Electrophilic Fluorination

Abstract: A novel and efficient route for the preparation of (2S)-2-chloro-2-fluorolactone 29 is described. This approach takes advantage of a highly efficient diastereoselective electrophilic fluorination reaction (94% yield; >50:1 dr).

Cited by 8 publications

References 43 publications

Bioactive secondary metabolites from new endophytic fungus Curvularia. sp isolated from Rauwolfia macrophylla

Bioactive secondary metabolites from new endophytic fungus Curvularia. sp isolated from Rauwolfia macrophylla

Diastereoselective Synthesis of 2′-Dihalopyrimidine Ribonucleoside Inhibitors of Hepatitis C Virus Replication

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

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