Divergent total synthesis of aspinolides B, E and J

Chang, Cai-Zhu; Geng, Jialin; Du, Yuguo; Lv, Qingwei; Dong, Zhi‐Bing; Li, Jun

doi:10.1016/j.tet.2019.06.015

Cited by 8 publications

(10 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Both the spectroscopic data ( 1 H, 13 C NMR and HRMS) of synthetic (+)-goniothalesdiol A (1) and (-)-parvistone E /leiocarpin A (2) are in good agreement with natural product and those of synthetic samples reported by other groups. 2,4,6,9 The optical rotation value for synthetic Previous studies indicated that some structurally similar styryllactones, such as the 9-deoxygoniopypyrone 18 and goniopypyrone 3 , exhibited strong antimalarial activity against plasmodium falciparum and potent anti-proliferation activity on cancer cell lines including Vero cell and NCI-H187 cells.…”

supporting

confidence: 84%

“…Using chromatographic pure methanol as solvent, high-resolution mass spectrometry data (HRMS) were recorded by ESI-QTOF mass spectrometer. 1 H NMR and 13 C NMR data were obtained by 400 MHz or 100 MHz nuclear magnetic resonance spectrometer. Chemical shift (δ) was expressed in ppm relative to the residual solvent, including chloroform and acetone.…”

Section: General Experimental Proceduresmentioning

confidence: 99%

“…1 H NMR (400 MHz, Chloroform-d) δ 7.45 -7.29 (m, 5H), 6.16 (ddd, J = 17.2, 10.4, 7.1 Hz, 1H), 5.49 (dd, J = 17.2, 1.2 Hz, 1H), 5.35 (dd, J = 10.2, 1.2 Hz, 1H), 4.76 (dd, J = 6.6, 6.0, 1.2 Hz, 1H), 4.68 (d, J = 8.6 Hz, 1H), 4.31 (dd, J = 8.6, 6.2 Hz, 1H), 1.48 (s, 3H), 1.32 (s, 3H). 13 C NMR (100 MHz, Chloroform-d) δ 141.2, 134.2, 128.4, 128.0, 127.1, 118.4, 108.9, 80.9, 78.9, 72.4, 27.9, 25.3. HRMS (ESI): calcd.…”

Section: Procedures Synthesis Of Compoundmentioning

confidence: 99%

See 2 more Smart Citations

Divergent Synthesis and Biological Evaluation of 2,6-Disubstituted Tetrahydropyran-Containing Natural Products: Parvistone E, Goniothalesdiol A, 6-epi-Goniothalesdiol A, and 8-epi-9-Deoxygoniopypyrone

Xie,

Liu,

Zhao

et al. 2023

Synthesis

Self Cite

View full text Add to dashboard Cite

A concise and efficient synthesis of (+)-goniothalesdiol A and (–)-parvistone E (leiocarpin A), as well as the first total synthesis of (–)-6-epi-goniothalesdiol A and (–)-8-epi-9-deoxygoniopypyrone acetate, has been achieved in 4 or 5 longest linear steps based on chiron approach. The potential biological activities of four 2,6-disubstituted tetrahydropyran-containing natural products were explored based on a panel of human cancer cell lines, BV-2 microglia and 3T3-L1 preadipocytes, respectively. Our results indicated that these four natural products displayed significant adipogenic activity in 3T3-L1 preadipocytes, but without obvious effects on cancer cell proliferation and LPS stimulated microglia activation.

show abstract

supporting

confidence: 84%

Section: General Experimental Proceduresmentioning

confidence: 99%

Section: Procedures Synthesis Of Compoundmentioning

confidence: 99%

See 1 more Smart Citation

Divergent Synthesis and Biological Evaluation of 2,6-Disubstituted Tetrahydropyran-Containing Natural Products: Parvistone E, Goniothalesdiol A, 6-epi-Goniothalesdiol A, and 8-epi-9-Deoxygoniopypyrone

Xie,

Liu,

Zhao

et al. 2023

Synthesis

Self Cite

View full text Add to dashboard Cite

show abstract

“…Liu, Dong, and co‐workers exposed the stereoselective synthesis of aspinolides B, E, and J ( 841 – 843) , these are characterized by 10‐membered lactone core (Scheme 131). [312] In this synthetic strategy, CM was one of the crucial steps, utilized to produce an alkene precursor 839 for these aspinolides. Wittig olefination and catalytic hydrogenation of D‐ribose derivate 835 yielded a diol 836 , which upon treatment with I 2 /PPh 3 /imidazole generated a terminal alkene derivative 837 .…”

Section: Cross Metathesis (Cm)mentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

View full text Add to dashboard Cite

The passion of total‐ and fragments syntheses of natural products always remained one of the top priorities among the synthetic chemists worldwide. Due their curiosity toward the complexity of molecules of living nature and their endeavour to imitate them in laboratory; limitless arrays of natural products have been extracted, architecturally‐elucidated, synthesized, and chronicled by utilizing various synthetic methodologies in different fashions. Frequently, the synthesis of complex natural products proceed with inscrutable synthetic challenges, which can be circumvented either by modification of previously developed synthetic methods or by formulating a new one. In this way, a myriad of powerful synthetic reactions have been developed since the genesis of the logic of chemical synthesis. Amongst them, metathesis tactics discovered unexpectedly in the 1950s (Nobel Prize in 2005), have incredibly influenced and changed the landscape of the art of the total and formal synthesis in the last three A. H. Hoveyda, A. R. Zhugralin, me abruptly as compared to other developed transformations or their modified forms. In this particular review article, we envisioned to report a comprehensive detail of the metathetic tools involved in both total and fragments synthesis of natural products in the years 2018 and 2019 along with an overview of 2017.

show abstract

“…23 Commercially available d -mannofuranose diacetonide 12 was easily converted into known benzoate 13 with benzoyl chloride in anhydrous pyridine. Selective hydrolysis of the terminal acetonide group of 13 with Amberlite IR-120 (H + ) ion-exchange resin in methanol gave diol 14 , which, upon exposure to excess amount iodine in refluxing toluene in the presence of imidazole and triphenylphosphine (TPP), 24 afforded the terminal alkene 10 . It is worth mentioning that the desired olefin 10 could be obtained from d -mannofuranose diacetonide ( 12 ) in good overall yield via three operations by a single chromatographic purification.…”

mentioning

confidence: 99%