Synthesis of new stable fluoroprostacyclin analogs with potent anti-anginal activity

Asai, Tomoyuki; Morizawa, Yoshitomi; Shimada, Toyomichi; Nakayama, Toshiaki; Urushihara, Masahiro; Matsumura, Yasushi; Yasuda, Arata

doi:10.1016/0040-4039(94)02217-y

Cited by 18 publications

(8 citation statements)

References 11 publications

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“…The synthesis of propargylic fluorides can be accomplished by the deoxyfluorination of propargylic alcohols with DAST146 or fluorination of a variety of activated propargylic substrates147 such as propargylic mesylates or silyl ethers. Other commonly used deoxofluorinating reagents for the synthesis of propargylic fluorides include SF 4 ,147a,b, 148 dialkylaminosulfur trifluorides,147c,d,f,g Yarovenko’s reagent (Figure 2),149 and Ghosez’s reagent ( N , N ‐diisopropyl‐1‐fluoro‐2‐methylpropenamine) 150. Grée and co‐workers achieved the synthesis of chiral propargylic fluorides through an S N 2 reaction between chiral, nonracemic propargylic alcohols and fluoride 151.…”

Section: Fluorinationmentioning

confidence: 99%

Introduction of Fluorine and Fluorine‐Containing Functional Groups

Liang¹,

Neumann²,

Ritter³

2013

Angew Chem Int Ed

2,269

856

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Over the past decade, the most significant, conceptual advances in the field of fluorination were enabled most prominently by organo‐ and transition‐metal catalysis. The most challenging transformation remains the formation of the parent CF bond, primarily as a consequence of the high hydration energy of fluoride, strong metal—fluorine bonds, and highly polarized bonds to fluorine. Most fluorination reactions still lack generality, predictability, and cost‐efficiency. Despite all current limitations, modern fluorination methods have made fluorinated molecules more readily available than ever before and have begun to have an impact on research areas that do not require large amounts of material, such as drug discovery and positron emission tomography. This Review gives a brief summary of conventional fluorination reactions, including those reactions that introduce fluorinated functional groups, and focuses on modern developments in the field.

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Section: Fluorinationmentioning

confidence: 99%

Introduction of Fluorine and Fluorine‐Containing Functional Groups

Liang¹,

Neumann²,

Ritter³

2013

Angew Chem Int Ed

2,269

856

View full text Add to dashboard Cite

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“…Thus, ethyl (R)-mandelate is converted into ethyl (S)-2-fluoro(phenyl)acetate [146]. Thus, ethyl (R)-mandelate is converted into ethyl (S)-2-fluoro(phenyl)acetate [146].…”

Section: Nucleophilic Fluorinating Reagentsmentioning

confidence: 99%

Organofluorine Compounds

Hiyama¹

2000

971

318

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“…Optimization studies using a model substrate showed that fluorination of the corresponding trimethylsilyl ether 62 with piperidinosulfur trifluoride gave the best yields. The fluorination of 7-( S )- 62 or 7-( R )- 62 led to the same product 7-( R )- 63 , indicating that the reaction proceeds via a common carbocationic intermediate, with the fluoride nucleophile approaching preferentially anti with respect to the bulky triethylsiloxy group (Scheme ). – …”

Section: Propargylic Fluoridesmentioning

confidence: 98%

“…Lindlar’s catalyst has also been used successfully in the partial hydrogenation of propargylic fluorides for the synthesis of analogues of fatty acid metabolites 90 , , fluorine-containing prostacyclin precursors 91 – and 3-fluoropurine ribonucleosides 92 (Scheme ).…”

Section: Propargylic Fluoridesmentioning

confidence: 99%