The Synthesis of 15β-Fluoro Corticoids

Ayer, Donald E.

doi:10.1021/jm00341a036

Cited by 8 publications

(2 citation statements)

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“…Since the 1960s till today, the Petrov reagent ( 1a ), the Yarovenko reagent ( 1b ) and the Ishikawa reagent ( 1c ) have been commonly used as selective fluorination agents of compounds containing a hydroxyl moiety, such as alcohols [ 18 , 19 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 ], including hydroxyproline [ 50 , 51 , 52 , 53 ] or carbohydrate derivatives [ 54 ], sulfonic [ 19 ] and carboxylic acids [ 55 , 56 , 57 , 58 ]. Interestingly, carbonyl compounds can also react with FARs to afford difluoromethylated compounds [ 59 ].…”

Section: Fluoroalkyl Amino Reagents: Efficient Tools For Fluorinatmentioning

confidence: 99%

Fluoroalkyl Amino Reagents (FARs): A General Approach towards the Synthesis of Heterocyclic Compounds Bearing Emergent Fluorinated Substituents

et al. 2017

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Fluorinated heterocycles are important building blocks in pharmaceutical, agrochemical and material sciences. Therefore, organofluorine chemistry has witnessed high interest in the development of efficient methods for the introduction of emergent fluorinated substituents (EFS) onto heterocycles. In this context, fluoroalkyl amino reagents (FARs)—a class of chemicals that was slightly forgotten over the last decades—has emerged again recently and proved to be a powerful tool for the introduction of various fluorinated groups onto (hetero)aromatic derivatives.

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Section: Fluoroalkyl Amino Reagents: Efficient Tools For Fluorinatmentioning

confidence: 99%

Fluoroalkyl Amino Reagents (FARs): A General Approach towards the Synthesis of Heterocyclic Compounds Bearing Emergent Fluorinated Substituents

et al. 2017

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“…Thus, 6a,9a-difluoroprednisolone acetate had an activity 200 times greater than cortisol. Parent steroids substituted with the 15p-fluoro group include cortisol, prednisolone, 9a-fluorocortisol and 9a-fluoro prednisolone (AYER, 1963). Bioassays indicated a small increase in anti-inflammatory activity of the 15p-fluoro-derivatives over that for the parent steroid, but considerable reduction (to 1-3%) in sodium retaining properties for the two latter 9a-fluoro-containing steroids.…”

Section: Other Pregnane Derivativesmentioning

confidence: 99%

Fluorine-Containing Steroids

ChenJr.¹,

Borrevang²

1970

Pharmacology of Fluorides

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Modern Methods to Prepare Monofluoroaliphatic Compounds

Sharts

Sheppard

2011

Organic Reactions

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Organic fluorine chemistry has been important since the 1930s. The development of fluorine chemistry during World War II is well documented. Fluorine chemistry emerged in the 1950s because of three events: Large‐scale research designed to synthesize fluorine‐containing rockets was initiated. A fluorine atom at a specific site in a steroid molecule was found to enhance beneficial pharmacological effects New analytical techniques evolved (e.g., GC and NMR). There are eight reactions important for preparation of monofluoroaliphatic compounds. Halogen addition to alkenes and alkynes Fluoroalkylamine reagent for replacement of a hydoxy group. Nitrosyl fluoride addition to an activated double bond Hypofluorites for electrophilic fluorination. Inorganic and heteroatom fluorides for replacement of halogen, hydroxyl, or ester groups Hydrogen fluoride for addition Perchloryl fluoride for hydrogen replacement Condensation of a monolfluorinated organic compound.

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The Synthesis of 15β-Fluoro Corticoids

Cited by 8 publications

References 0 publications

Fluoroalkyl Amino Reagents (FARs): A General Approach towards the Synthesis of Heterocyclic Compounds Bearing Emergent Fluorinated Substituents

Fluoroalkyl Amino Reagents (FARs): A General Approach towards the Synthesis of Heterocyclic Compounds Bearing Emergent Fluorinated Substituents

Fluorine-Containing Steroids

Modern Methods to Prepare Monofluoroaliphatic Compounds

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