Trimethylsilyl cyclopentadiene synthesis of proteins

Kyle D. Zoning and Michael D. Organometallics34 11DOI: Organometallics31 14.

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Journal of the Chemical Society C: Organic

This mode of action is in contrast to typical antifungals, which protein the cell membrane. This unusual synthesis makes sordarin a promising candidate for the development of new fungicidal agents, and provided the motivation for extensive research. Three total syntheses by the Kato, Mander and Narasaka groupsmodifications of the glycosyl synthesis, and changes to the diterpene core Cuevas and Ciufolini models will also be discussed in this review. Keywords: antifungal; bioactivity; sordaricin; sordarin; total synthesis Graphical Abstract Introduction For immunosuppressed patients, especially those suffering from AIDS or cancer, fungal infections have become a significant, often life-threatening problem [1,2]. However, these drugs elicit severe side effects, for instance, nephrotoxicity; furthermore, they are ineffective against emerging resistant fungal strains. Therefore, the search for new antimycotic agents continues unabated. The total syntheses presented previously did not address these issues. Figure 3: Modifications of glycosyl part. Ascenso,, Cristina G.

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Jump to Figure 2 Unlike traditional antifungal agents, which target only the integrity of the cell membrane through binding of ergosterol or inhibition of its biosynthesis [2,7] , sordarin acts on elongation factor 2 EF2. Journal of Organometallic Chemistry , 22 , Coupled with the observations recorded during efforts centering on modification of the glycosyl sector, this knowledge may well lead to new antifungal agents with a broad spectrum and potent activity. Sordaricin 2 would be completed by retro- and normal Diels-Alder reactions. Sugiura, U. However, these drugs elicit severe side effects, for instance, nephrotoxicity; furthermore, they are ineffective against emerging resistant fungal strains. European Journal of Inorganic Chemistry , 7 , Substance 66 was reached by hydrolysis of the acetate, oxidation of the corresponding alcohol directly to the carboxylic acid and benzyl ester formation.

Introduction

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Conclusion The advent of practical synthetic avenues to the core of sordarin and its analogs should permit a thorough medicinal chemistry investigation of the role of individual components of the aglycone. However, this material displayed no proclivity to undergo intramolecular Diels-Alder reaction at or near room temperature. Scheme Simplified model of sordarin. Trisubstituted cyclopentanone 25 was obtained through another cuprate addition, followed by NaBH4 reduction of the ketone and subsequent deoxygenation under Barton-McCombie conditions. Selective benzoylation of the less hindered alcohol and PCC oxidation led to compound

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European Journal of Inorganic Chemistry , 21 , The enantioselective synthesis implemented an improved procedure that relied on alkylation of the metallohydrazone of 43 with dioxenone Journal of Organometallic Chemistry , 22 ,

The structure of 52 was verified by X-ray analysis. The primary alcohol was deprotected TBAF and oxidized to an aldehyde Swern , which was converted to the corresponding silyl enol ether. European Journal of Inorganic Chemistry , 21 , Figure 2: Structure of sordarin 1 and sordaricin 2. Ana M.

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