Isolation of 1-.BETA.-D-Arabinofuranosylcytosine from the Mushroom Xerocomus nigromaculatus HONGO.

Takahashi, Akira; Nunozawa, Tetsuji; Endo, Takeshi; Nozoe, Shigeo

doi:10.1248/cpb.40.1313

Cited by 10 publications

(5 citation statements)

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“…The synthetic trazodone hydrochloride is far less likely to be present in the mushrooms since it is not a natural product. However, motifs and chemical structures with similarity to synthetic compounds have been found to be naturally occurring in other fungi ( 71 ), so the possibility that some fungal natural products could mimic the known function of these synthetic compounds is not unreasonable. Even if these two compounds were incorrectly identified, these results clearly demonstrate that additional chemicals in the metabolome of P. cubensis have real potential to contribute to physiological and neurological activity if consumed.…”

Section: Discussionmentioning

confidence: 99%

DNA Authentication and Chemical Analysis of Psilocybe Mushrooms Reveal Widespread Misdeterminations in Fungaria and Inconsistencies in Metabolites

Bradshaw

Backman

Ramírez-Cruz

et al. 2022

Appl Environ Microbiol

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Section: Discussionmentioning

confidence: 99%

DNA Authentication and Chemical Analysis of Psilocybe Mushrooms Reveal Widespread Misdeterminations in Fungaria and Inconsistencies in Metabolites

Bradshaw

Backman

Ramírez-Cruz

et al. 2022

Appl Environ Microbiol

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“…In 1992, the oxidative dimerization of propargyl alcohol using catalytic amounts of both Pd(PPh 3 ) 2 Cl 2 and CuI was achieved by Nozoe and co-workers (Scheme 24a ). 42 The reaction afforded 2,4-hexadiyne-1,6-diol as a precursor for the total synthesis of repandiol, a cytotoxic diepoxide. Later, ethynyltrimethylsilane was dimerized by Marder’s group to give the corresponding 1,3-diyne under similar catalytic conditions (Scheme 24b ).…”

Section: Oxidative Homo-dimerization Of Terminal Alkynes For the Synt...mentioning

confidence: 99%

Palladium-Catalyzed Homo-Dimerization of Terminal Alkynes

et al. 2023

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The palladium-catalyzed homo-dimerization of terminal alkynes is a powerful and atom economic method for the preparation of highly unsaturated four carbon skeletons, which are key structural units found in natural and/or biologically active products and materials. In homo-dimerization of terminal alkynes, a major issue is the control of chemo-, regio-, and stereoselectivity. For this effort, over the past few decades, various strategies and methods have been developed in palladium catalytic systems. Herein, we highlight prominent methods for the selective synthesis of these valuable compounds including conjugate 1,3-enynes, 1,3-diynes, and 1,3-dienes. 1 Introduction 2 Redox-Neutral Homo-Dimerization of Terminal Alkynes to 1,3-Enynes 2.1 Head to Head Dimerization 2.2 Head to Tail Dimerization 3 Oxidative Homo-Dimerization of Terminal Alkynes to 1,3-Diynes 3.1 Unsupported Palladium Catalysts 3.1.1 Choice of Oxidant 3.1.2 Choice of Ligand 3.1.3 Choice of Solvent 3.2 Supported Palladium Catalysts 4 Reductive Homo-Dimerization of Terminal Alkynes to 1,3-Dienes 5 Conclusion

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“…16 17 Ever since, Glaser coupling has become a simple and reliable method for the synthesis of symmetrical 1,3-diynes. 18,19 Not only as synthetic intermediates, the importance of symmetrical 1,3-diynes is manifested by their occurrence in bioactive natural products, 20 synthetic drug analogues, 21 and π-materials 22 (Figure 1 ).…”

Section: Table 1 Optimization Of Reaction Parameters Wi...mentioning

confidence: 99%

Synthetic Access to 1,3-Butadiynes via Electro-redox Cuprous-Catalyzed Dehydrogenative Csp–Csp Homocoupling of Terminal Acetylenes

Kathiresan,

Praveen,

Krishnan

2023

Synthesis

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Herein, we disclose the oxidative homocoupling of terminal alkynes under electrochemically generated cuprous catalysis. The scope of this protocol was established by preparing an array of structurally and electronically different 1,3-butadiyne derivatives. Good synthetic yields, functional group tolerance, oxidant-free conditions, and no cross-selectivity are some of the intrinsic advantages of this methodology. The developed chemistry features the electro-redox formation of copper acetylide, an intermediate appropriate for the Csp–Csp coupling step. The chemical state of copper in the acetylide intermediate was found to be Cu(I), as confirmed by click trapping experiments, cyclic voltammetry, EPR spectroscopy, and XPS. A competition reaction to determine the reactivity of electronically dissimilar acetylenes revealed that the product ratio is rather dependent on the electronic nature of the alkynyl substituents. To highlight the synthetic value of the products, selected diynes were subjected to chemical diversification.

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Isolation of 1-.BETA.-D-Arabinofuranosylcytosine from the Mushroom Xerocomus nigromaculatus HONGO.

Cited by 10 publications

References 0 publications

DNA Authentication and Chemical Analysis of Psilocybe Mushrooms Reveal Widespread Misdeterminations in Fungaria and Inconsistencies in Metabolites

DNA Authentication and Chemical Analysis of Psilocybe Mushrooms Reveal Widespread Misdeterminations in Fungaria and Inconsistencies in Metabolites

Palladium-Catalyzed Homo-Dimerization of Terminal Alkynes

Synthetic Access to 1,3-Butadiynes via Electro-redox Cuprous-Catalyzed Dehydrogenative Csp–Csp Homocoupling of Terminal Acetylenes

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