Phosphine-catalyzed divergent domino processes between γ-substituted allenoates and carbonyl-activated alkenes

Wu, Mingyue; Han, Zhaobin; Ni, Huanzhen; Wang, Nengzhong; Ding, Kuiling; Lü, Yixin

doi:10.1039/d1sc06364b

Cited by 16 publications

(4 citation statements)

References 105 publications

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“…First, 1 was dissolved in THF and hydrolyzed by HCl solution. The crude product was further purified by silica gel CC to obtain pure products 3 and 4 [ 29 ]. Then, 1 was dissolved in THF and H 2 O, the hydrolysis condition was changed to alkaline KOH solution, and the reaction was at 0 °C for 2 h to prepare the pure product 5 .…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Anti-Hepatocellular Carcinoma Evaluation of Sesquiterpene Lactone Epimers Trilobolide-6-O-isobutyrate Analogs

Zhou,

Yi,

Qian

et al. 2024

Molecules

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Hepatocellular carcinoma (HCC), one of the most common malignant cancers with a low 5-year survival rate, is the third leading cause of cancer-related deaths worldwide. The finding of novel agents and strategies for the treatment of HCC is an urgent need. Sesquiterpene lactones (SLs) have attracted extensive attention because of their potent antitumor activity. In this study, a new series of SL derivatives (3–18) were synthesized using epimers 1 and 2 as parent molecules, isolated from Sphagneticola trilobata, and evaluated for their anti-HCC activity. Furthermore, the structures of 4, 6, and 14 were confirmed by X-ray single-crystal diffraction analyses. The cytotoxic activities of 3–18 on two HCC cell lines, including HepG2 and Huh7, were evaluated using the CCK-8 assay. Among them, compound 10 exhibited the best activity against the HepG2 and Huh7 cell lines. Further studies showed that 10 induced cell apoptosis, arrested the cell cycle at the S phase, and induced the inhibition of cell proliferation and migration in HepG2 and Huh7. In addition, absorption, distribution, metabolism, and excretion (ADME) properties prediction showed that 10 may possess the properties to be a drug candidate. Thus, 10 may be a promising lead compound for the treatment of HCC.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Anti-Hepatocellular Carcinoma Evaluation of Sesquiterpene Lactone Epimers Trilobolide-6-O-isobutyrate Analogs

Zhou,

Yi,

Qian

et al. 2024

Molecules

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“…In 2022, Lu and co-workers developed a phosphinecatalysed chemodivergent domino reaction using γ-substituted allenoates 100 and activated alkenes (Scheme 32a). [74] The allenoates have provided the bicyclic furofurans 138 upon reaction with triketone enone 137 under NUSIOC-Phos 117 catalysis. The bicyclic acetals were delivered in good yields with high stereoselectivities (40-90%, up to > 20 : 1 dr, 85-99% ee).…”

Section: Enantioselective Annulation Reactions Of δ-Aryl (Alkyl) Alle...mentioning

confidence: 99%

Asymmetric Organocatalytic Reactions of Activated Racemic Allenes

et al. 2022

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Asymmetric organocatalytic reactions of various electron-deficient racemic allenes with a wide variety of nucleophiles and electrophiles were reviewed. The literature on enantioselective functionalization of allenes that employs chiral phosphine, amine, phase transfer, bifunctional, and Brønsted acid catalysis is presented along with the mecha-nisms. In addition, the review emphasizes methods of obtaining enantioenriched allenes from racemic allenes via organocatalytic (dynamic) kinetic resolution techniques. The synthetic utility of the developed methodologies toward the target-orientated biologically active molecules is narrated along with the examples.

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“…For instance, the Wu group reported an Et 3 N-mediated bicyclization of triketone enones with malononitrile for the synthesis of fused furofuran compounds in 2013 (Scheme A). Recently, the Lu group developed a phosphine-catalyzed domino transformation of triketone enones with γ-substituted allenoates to form bicyclic furofurans in good yields with excellent enantioselectivities (Scheme B). Very recently, our group disclosed CPA-catalyzed regio-reversed domino processes of triketone enones with azlactones, giving a variety of bicyclic furofurans bearing vicinal quaternary carbons with good enantioselectivities (Scheme C).…”

Section: Introductionmentioning

confidence: 99%

Diastereodivergent and Regioselective Synthesis of Tetrahydrofuro[2,3-b]furans with Four Consecutive Stereocenters

Zhang,

Sun,

Jiang

et al. 2024

J. Org. Chem.

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Base-catalyzed diastereodivergent and regioselective domino processes of triketone enones with arylacetaldehydes for the synthesis of tetrahydrofuro[2,3-b]furans with four consecutive stereocenters are reported. Good yields and diastereoselectivities are obtained when DBU is employed as a catalyst; in contrast, Et 3 N delivers a different diastereomer in excellent diastereoselectivity. This work offers many advantages, including switchable diastereoselectivity, cheap base catalysts, and a simple operation.

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Phosphine-catalyzed divergent domino processes between γ-substituted allenoates and carbonyl-activated alkenes

Abstract: Highly enantioselective and chemodivergent domino reactions between g-substituted allenoates and activated alkenes have been developed. In the presence of NUSIOC-Phos, triketone enone substrates smoothly reacted with γ-substituted allenoates to form...

Cited by 16 publications

References 105 publications

Design, Synthesis, and Anti-Hepatocellular Carcinoma Evaluation of Sesquiterpene Lactone Epimers Trilobolide-6-O-isobutyrate Analogs

Design, Synthesis, and Anti-Hepatocellular Carcinoma Evaluation of Sesquiterpene Lactone Epimers Trilobolide-6-O-isobutyrate Analogs

Asymmetric Organocatalytic Reactions of Activated Racemic Allenes

Diastereodivergent and Regioselective Synthesis of Tetrahydrofuro[2,3-b]furans with Four Consecutive Stereocenters

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