An asymmetric synthesis of (+)-Scrodentoid A from dehydroabietic acid

Song, Yi-Kang; Liu, Li; Wang, Junjie; Qian, Fei; Yang, Mao-Qi; Zhang, Liuqiang; Fu, Jian‐Guo; Li, Yiming; Feng, Chen‐Guo

doi:10.1016/j.tet.2021.132031

Cited by 5 publications

(5 citation statements)

References 28 publications

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“…As shown in Figure A–E, cyclopropanecarboxylate ester 42 showed better antitumor activity than nepetaefolin F in gastric cancer, ovarian cancer, breast cancer, lung cancer, and liver cancer cell lines, especially in MGC 803 cells. In our previous research, nepetaefolin F showed good antitumor activity (IC 50 was 6.3 μM) in a patient-derived xenograft (PDX) model of non-small-cell lung cancer (LUPF045); however, it showed low cytotoxicity to A549 cells in our study. Non-small-cell lung carcinoma includes squamous cell carcinoma, adenocarcinoma, and large-cell carcinoma.…”

Section: Resultscontrasting

confidence: 52%

“…Commercially available dehydroabietic acid ( 10 ) has been widely used as the precursor for the synthesis of natural abietane analogues by medicinal chemists. − As outlined in Scheme , nepetaefolin F ( 5 ) could be assembled from aldehyde 8 through α-methylation of aldehyde. Hydroboration–oxidation of allylic alcohol 9 would be able to deliver aldehyde 8 .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Bioactivity Evaluation of Nepetaefolin F and Its Analogues

Mao

et al. 2023

ACS Omega

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Nepetaefolin F (5), an abietane diterpenoid, showed significant inhibitory activity against human cancer cells in vitro with an IC 50 value of 6.3 μM. The syntheses of nepetaefolin F and its analogues are presented herein. The cytotoxicity against various cancer cell lines was evaluated; notably, the cyclopropanecarboxylate ester 42 displayed significant antitumor activity against MGC 803 cells with an IC 50 value of 20.9 μM. Further studies revealed that 42 could upregulate the expression of p62, microtubule-associated protein 1 light-chain 3 β (LC3 B-I), cleaved caspase-3, and cleaved caspase-9 and downregulate the expression of Beclin-1 and LC3B-II. Kyoto Encyclopedia of Genes and Genomes (KEGG) analysis showed that 42 could modulate multiple signaling pathways, especially for peroxisome proliferator-activated receptor (PPAR) and AMP-activated protein kinase (AMPK), which are closely related to autophagy. These results suggested that compound 42 is a promising lead by inhibiting cell proliferation and autophagy, as inducing cell apoptosis in MGC 803 cells.

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Section: Resultscontrasting

confidence: 52%

Section: Resultsmentioning

confidence: 99%

Synthesis and Bioactivity Evaluation of Nepetaefolin F and Its Analogues

Mao

et al. 2023

ACS Omega

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“…Compound 1g was decomposed (Table S7, entries 1–3), so as compound 1d (Table S7, entries 4 and 5). Fortunately, compound 1h was successfully prepared in 96% yield when NaSEt was used as an appropriate demethylation reagent in this reaction − (Scheme ). After the Davis oxidation of 1h and Wacker oxidation of 1i in sequence, the first total synthesis of (±)-guignardin A ( 1 ) was completed in 14.9% overall yield in seven steps from 5-methoxy-1-tetralone 1a .…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis and Biological Activity of (±)-Guignardin A, (±)-Palmarumycin B₉, and Their Derivatives

Xu,

Ma,

et al. 2024

ACS Agric. Sci. Technol.

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A strategy for constructing an α-hydroxyl-α-acetonyl moiety was described for the total synthesis of guignardin A (1), 8-deoxypalmarumycin B 9 (2), and palmarumycin B 9 (3) via 7-, 8-, and 11-step reactions in 14.9, 1.5, and 0.4% overall yields from 5methoxy-1-tetralone (1a), chroman-4-one (2a), and 2,5-dimethoxybenzaldehyde (3a) as the starting materials, respectively. The key steps included AlCl 3 -or NaSEt-mediated demethylation, Davis oxidation, and Wacker oxidation. Their structures were characterized by 1 H and 13 C NMR, HR-ESI-MS, and X-ray diffraction data. A series of spiromamakone A monobenzo derivatives were designed and synthesized by three diallyl-substituted byproducts via olefin metathesis as the key step. The antifungal investigation indicated that compounds 1l and 2n exhibited excellent inhibitory activities against phytopathogen Rhizoctonia solani with EC 50 values of 8.68 and 5.25 μg/mL, respectively. Compound 2n had the destructive and inhibitory effects on the morphology and growth of the hyphae of R. solani.

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“…Cyclic diacyl peroxides are utilized in dihydroxylation, dioxygenation [17][18][19][20][21][22][23], and oxyamination [24] of alkenes. Oxyfunctionalization of arenes [25][26][27][28][29][30][31] as well as arene dearomatization [32] were achieved using these peroxides. Oxidative acyloxylation of dicarbonyl compounds [33], heterocycles [34], and the derivatives of monocarbonyl compounds [35,36] also were developed.…”

Section: Resultsmentioning

confidence: 99%

1-(((6-(Methoxycarbonyl)-5-oxononan-4-yl)oxy)carbonyl)cyclopropane-1-carboxylic Acid

Gorlov

Shuingalieva

Ilovaisky

et al. 2023

Molbank

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Here, we first report the 2′-acyloxy-1,3-dicarbonyl compound construction in a three-component oxidative reaction of alkyl ketene dimer with cyclic diacyl peroxide and trimethyl orthoformate. The discovered synthesis allows us to form 2′-functionalized 1,3-dicarbonyl compounds instead of the common 2-functionalized moiety. The reaction between 4-butylidene-3-propyloxetan-2-one and cyclopropyl malonoyl peroxide proceeds in the presence of trifluoroacetic acid and trimethyl orthoformate at 120 °C for 1 h. The synthesized compound was characterized by NMR spectroscopy, mass spectrometry, and IR spectroscopy.

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An asymmetric synthesis of (+)-Scrodentoid A from dehydroabietic acid

Cited by 5 publications

References 28 publications

Synthesis and Bioactivity Evaluation of Nepetaefolin F and Its Analogues

Synthesis and Bioactivity Evaluation of Nepetaefolin F and Its Analogues

Total Synthesis and Biological Activity of (±)-Guignardin A, (±)-Palmarumycin B₉, and Their Derivatives

1-(((6-(Methoxycarbonyl)-5-oxononan-4-yl)oxy)carbonyl)cyclopropane-1-carboxylic Acid

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An asymmetric synthesis of (+)-Scrodentoid A from dehydroabietic acid

Cited by 5 publications

References 28 publications

Synthesis and Bioactivity Evaluation of Nepetaefolin F and Its Analogues

Synthesis and Bioactivity Evaluation of Nepetaefolin F and Its Analogues

Total Synthesis and Biological Activity of (±)-Guignardin A, (±)-Palmarumycin B9, and Their Derivatives

1-(((6-(Methoxycarbonyl)-5-oxononan-4-yl)oxy)carbonyl)cyclopropane-1-carboxylic Acid

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Total Synthesis and Biological Activity of (±)-Guignardin A, (±)-Palmarumycin B₉, and Their Derivatives