Carbocycloaddition strategies for troponoid synthesis

Murelli, Ryan P.; Berkowitz, Alex J.; Zuschlag, Daniel W.

doi:10.1016/j.tet.2022.133175

Cited by 11 publications

(4 citation statements)

References 148 publications

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“…Tropones, a class of non-benzenoid aromatic compounds, have been found in numerous natural products, showing distinct biological activities [1][2][3][4][5]. Aryl-annulated tropone derivatives such as benzotropones [6][7][8][9][10][11][12][13][14][15][16][17] and furotropones [18][19][20][21][22][23] are also attractive molecules because their extended conjugations might exhibit intriguing chemical and photophysical properties (Figure 1A).…”

Section: Introductionmentioning

confidence: 99%

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Preparation of Dibenzofurotropones via Pd-Catalyzed Cyclization

Lin,

Liu

2024

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A synthetic approach to dibenzofurotropone derivatives 1 has been developed through the palladium-catalyzed cyclization of (2-bromoaryl)(3-arylfuran-2-yl)methanones 2 via the activation of arylic C–H bonds. Compounds 2 were easily prepared from the palladium-promoted acyl migration and cyclization of (Z)-pent-2-en-4-yn-1-yl acetates 3 in the presence of 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU), followed by oxidative decarbonylation and oxidation with O2. Ten new tropone compounds are reported and these compounds show absorption in the UV-vis region and emission in the visible region.

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Section: Introductionmentioning

confidence: 99%

“…Pd(OAc)2/PCy3•HBF4 Cs2CO3 (1.2) toluene 110 °C/20 h - 1 Reaction conditions: A mixture of 2aa (0.2 mmol), [Pd] (10 mol%), ligand (20 mol%) and base solvent (2 mL) was heated in an oil bath under N2. 2 NMR yields. 3 Under air atmosphere.…”

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confidence: 99%

Preparation of Dibenzofurotropones via Pd-Catalyzed Cyclization

Lin,

Liu

2024

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“…Currently, the applications of substituted tropones are significantly limited by their preparative methods. The known methods for the synthesis of substituted tropones mainly include oxidation of seven-membered carbocycles, cyclization, ring expansion, and carbocycloaddition. , In general, these methods employ substrates prepared in multiple steps, require transition metals, and/or exhibit narrow substrate scope, low yields, and/or poor site selectivity.…”

Section: Introductionmentioning

confidence: 99%

Access to 2-Alkyltropones via Organic Base-Catalyzed Tandem Deamination and Aldol Condensation of Tropinone-Derived Quaternary Ammonium Salts

Wang,

Wu,

Tian

2023

J. Org. Chem.

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The tropone skeleton exists in a number of natural products and bioactive substances, and currently, the applications of substituted tropones are significantly limited by their preparative methods. Herein, we report a very convenient method to access 2-alkyltropones via organic base-catalyzed tandem reaction of tropinone-derived quaternary ammonium salts. Tropinone methiodide reacted with a wide variety of aromatic and aliphatic aldehydes in the presence of 1,4-diazabicyclo[2.2.2]octane to afford structurally diverse 2-alkyltropones in moderate to excellent yields with extremely high site selectivity. The reaction employs readily available feedstocks and reagents, is free of transition metals and compatible with water and air, tolerates a variety of functional groups, and can be easily scaled up. Moreover, the products are amenable to various synthetic transformations. Preliminary mechanistic studies revealed that the reaction proceeded via tandem deamination, aldol condensation, and isomerization.

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“…To date, the synthetic routes to substituted tropones mainly include oxidation of seven-membered carbocycles, 6 cyclization, 7 ring expansion, 8 and carbocycloaddition. 9,10 Nevertheless, these methods generally employ substrates prepared in multiple steps, require transition metals, exhibit narrow substrate scope, and/or suffer from poor site selectivity.…”

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confidence: 99%