1-Fluorocycloalkanecarboxylic Acids in the Synthesis of 16-Achiral 16-Fluoro-9a-carbaprostacyclin Derivatives

Mongelli, Nicola; Animati, Fabio; D’Alessio, Roberto; Zuliani, L.; Gandolfi, C.

doi:10.1055/s-1988-27551

Cited by 14 publications

(4 citation statements)

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“…The crude mixture was concentrated in vacuo and chromatographed on silica gel (ether:hexane 1:9) to give 2,3-epoxy-3-methyloctanenitrile ( 7 ) (5.217 g, 68.2%) as a colorless oil. These data are consistent with published data …”

Section: Methodssupporting

confidence: 94%

“…Intrigued by this result, we wanted to see how general this new rearrangement methodology was for other alkyl-, alkenyl-, or aryl-substituted epoxynitriles. A selection of epoxynitriles 7 − 12 were synthesized (Table ) according to the methods of Stork, Svoboda, or Mongelli . In the case of epoxynitrile 10 the reported method (solid NaOH) was too slow in our hands to be practical, therefore the method implemented by Stork was used.…”

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confidence: 99%

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Rearrangement of Epoxynitriles: A Convenient Homologation of Acyclic and Cyclic Ketones to Carboxylic Acids

Badham

Mendelson

et al. 2002

J. Org. Chem.

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A convenient two-step homologation of both aliphatic and aromatic ketones to the corresponding carboxylic acid has been developed. First ketones were converted to epoxynitriles with the Darzens reaction. Second, a Lewis acid mediated rearrangement of these epoxynitriles with lithium bromide was achieved to give homologated secondary alkanoic acids (as well as aryl-alkanoic) in good yields. The mechanism and the scope of the rearrangement reaction were investigated. This strategy constitutes a two-step homologation of ketones to secondary carboxylic acids.

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Section: Methodssupporting

confidence: 94%

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confidence: 99%

Rearrangement of Epoxynitriles: A Convenient Homologation of Acyclic and Cyclic Ketones to Carboxylic Acids

Badham

Mendelson

et al. 2002

J. Org. Chem.

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“…Later in the 1980s, cyanohydrins 15 or the corresponding αhydroxy esters were obtained in a similar fashion from spirocyclic glycidonitriles (14) and glycidic esters, respectively, and used to synthesize several α-fluorocycloalkyl building blocks, e. g. carboxylic acid 17, [38] amino acids 18, [39][40][41] αketoacids 19, [42] or derivatives thereof [41,43] (Scheme 6).…”

Section: Chemmedchemmentioning

confidence: 99%

Fluorinated Cycloalkyl Building Blocks for Drug Discovery

et al. 2022

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The review covers various aspects of fluorinated cycloalkyl (C3−C7) building blocks for drug discovery, including their synthesis, key physicochemical properties, and biological and medicinal applications of their derivatives. The discussed synthetic methods include classical nucleophilic fluorinations of various substrates, the addition of fluorine and another heteroatom to double bonds, cycloadditions and other transformations of fluorine‐containing substrates, as well as some newer reactions like fluorination of non‐activated and remotely activated C−H bonds, decarboxylative and deborylative fluorinations, etc. The known data on the effect of introducing the fluorinated cycloalkyl groups on the compound's key in vitro parameters (such as acidity/basicity, lipophilicity, conformational behavior, and short contact capabilities) are surveyed. Finally, applications of fluorinated cycloalkyl building block derivatives in the design of biologically active compounds (including marketed drugs Maraviroc, Ivosidenib, and Sitafloxacin) are covered, with a focus on the fluorination impact.

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“…Nitriles and esters of glycidic acids (glycidonitriles and glycidates) are useful substrates for the preparation of a variety of important products, such as carbonyl compounds, 1,2 carboxylic acids, 3 fluorine-substituted carboxylic acids, [4][5][6] cyanodioxolanes, 7 aziridine carboxylic esters 8 and cyanodienes. 9 Chemical transformations of alkenylsubstituted glycidonitriles and glycidates, however, have only rarely been investigated.…”

mentioning

confidence: 99%