Oxidation of furans. 2. Synthesis and biological properties of 6-hydroxy-2H-pyran-3(6H)-ones and derivatives

Laliberté, Réal; Medawar, G.; Lefebvre, Y.

doi:10.1021/jm00268a004

Cited by 67 publications

(12 citation statements)

References 3 publications

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“…Just shortly after the first reports on the halogenative ring expansion protocols by Cavill 9 and Achmatowicz, 10 an alternative procedure was introduced by Lefebvre and coworkers in 1972 using organic peracids as terminal oxidant. 43,44 Both m-chloroperbenzoic acid (MCPBA) as well as peracetic acid in chlorinated solvents proved to be excellent oxygenating agents in the Achmatowicz-type ring expan-…”

Section: Epoxidizing Agentsmentioning

confidence: 99%

The Achmatowicz Rearrangement – Oxidative Ring Expansion of Furfuryl Alcohols

2015

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Over the years, the oxidative ring enlargement of furfuryl alcohols, known as the Achmatowicz reaction, has been developed into a powerful and versatile synthetic tool for the preparation of 6-hydroxypyranones. This review provides a comprehensive collection of the various ways to perform Achmatowicz rearrangement reactions and explores the role of this ring-expansion process in contemporary organic synthesis. 1 Introduction 2 Classical Methods and Variants 3 Single-Electron-Transfer Oxidations 4 Metal-Catalyzed Ring Expansions 5 Photolytic Oxygenations 6 Enzymatic Transformations 7 Conclusions

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Section: Epoxidizing Agentsmentioning

confidence: 99%

The Achmatowicz Rearrangement – Oxidative Ring Expansion of Furfuryl Alcohols

2015

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“…For the practical demonstration of the use of 2 H ‐pyran‐3(6 H )‐ones 9 as key intermediates with great potential for diversification we carried out a significant number of derivatizations and transformations (Scheme ). Upon treatment with isocyanates they were converted into carbamates 10 , scaffolds known to show anticoccidial and antimicrobial activities 8a. b These carbamates were treated with further alcohols to give bioactive ethers 11 by using catalytic HClO 4 or, under alkaline conditions, quantitatively converted into pharmacophoric oxazolediones 12 10.…”

Section: Structures Cleavage Conditions Yields and Purity Of Selecmentioning

confidence: 99%

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Couladouros

Strongilos

2002

Angew. Chem.

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During the last decade we have witnessed the emergence of combinatorial chemistry as a tool for the discovery of new lead compounds. [1] Outstanding examples of sophisticated directed libraries have been reported, including pharmacophoric scaffolds, [2] bioactive metabolites, [2] designed ™unnatu-ral∫, diversity-oriented, pharmacophore-like, rigid, and versatile structures, [3] and even natural products with highly complex architectures. [4] The state-of-the-art in this field combines three main features: 1) suitably functionalized druglike ™privileged structures∫ [5] having specific spatial architecture and rigidity, 2) short synthetic pathways comprising reliable, clean, and high-yielding reactions, and 3) an overall ™diversification strategy∫ resulting ideally in ™libraries of libraries∫ [6] of scaffolds resembling evolution-selected molecules like natural products or drugs.Libraries are mainly based on a core molecule that is subjected to functional group manipulation which leads to a number of derivatives with the same central structure. Several versatile molecules that were key intermediates used by traditional medicinal chemists, for example, Corey©s lactone, the Wieland±Miescher ketone, and the Prelog±Djerassi lactone, could lead to a variety of apparently unrelated pharmacophoric frameworks. These starting materials are small molecules equipped with many reactive sites and functionalities, which can undergo both skeletal rearrangements and functional group interconversions. The use of such a polymorphic compound as the cornerstone of a library would be of great advantage since: 1) Many known synthetic key intermediates lead to medicinally important or ™privi-leged∫ scaffolds; 2) they possess high potential for both structural and functional diversification; 3) their chemical transformations and modifications in solution are well documented; and 4) the pharmacological activity of their descending structures is well precedented.To demonstrate the above concept, 2H-pyran-3(6H)-one (1) [7,8] was selected from among several synthetic key intermediates listed in the literature. As shown in Figure 1, derivatives of pyranone 1 exhibit significant biological activities, including antibacterial, antifungal, anticoccidial, antiinflamatory, and anticancer properties. Besides serving as intermediates in several natural product syntheses, such ZUSCHRIFTEN

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“…1 Furthermore, they are readily accessible and highly reactive, making them one of the most versatile synthons in organic synthesis. 2 For example, furans can be readily oxidized by reagents such as singlet oxygen, 3 m-CPBA, 4 NBS, 5 Oxone-KBr, 6 etc. to access a number of valuable four-carbon building blocks, depending on the substitution pattern.…”

Section: Introductionmentioning

confidence: 99%

Alkyne-Forming Furan Fragmentation: A General Method to Convert Furans into Alkynoic Acids

Deng

Gui

2019

Synlett

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Furans are readily available and highly reactive heterocycles that serve as versatile four-carbon synthons in organic synthesis. Recently, we discovered that furans, upon oxidation with singlet oxygen, can be transformed into alkynes via dual C–C double-bond cleavage. This Synpacts article presents an overview of the historical context and the development of this furan fragmentation reaction. We also discuss its application in natural product synthesis and a plausible reaction mechanism.1 Introduction2 Background of Alkyne-Forming Furan Fragmentation3 Reaction Development4 Conclusion

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Oxidation of furans. 2. Synthesis and biological properties of 6-hydroxy-2H-pyran-3(6H)-ones and derivatives

Cited by 67 publications

References 3 publications

The Achmatowicz Rearrangement – Oxidative Ring Expansion of Furfuryl Alcohols

The Achmatowicz Rearrangement – Oxidative Ring Expansion of Furfuryl Alcohols

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Alkyne-Forming Furan Fragmentation: A General Method to Convert Furans into Alkynoic Acids

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