Construction of the Tetracyclic Core of Calyciphylline B-Type <i>Daphniphyllum</i> Alkaloids

Du, Chenglong; Fang, Jiwen; Chen, Jinyan; Liu, Zaimin; Li, Huilin; Wang, Xiaolei; Xie, Xingang; She, Xuegong

doi:10.1021/acs.orglett.9b03322

Cited by 10 publications

(4 citation statements)

References 45 publications

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“…To date, some Daphniphyllum alkaloids from Daphniphyllaceae have been shown to possess cytotoxicity. [ 11,19‐20 ] Therefore, compounds 1 , 2 , 4 — 13 were evaluated for the cytotoxic activities against nasopharyngeal carcinoma (NPC) cells (CNE1 and CNE2) by MTT assay (Table 3). Among them, compound 1 ( N‐1 ) exhibited significant inhibitory effects on the proliferation of both CNE1 and CNE2 cells with IC 50 values of 9.3 ± 0.5 and 12.7 ± 0.6 μM (Figure 6A, B), respectively.…”

Section: Resultsmentioning

confidence: 99%

Dcalycinumines A—E, Alkaloids with Cytotoxic Activities of Nasopharyngeal Carcinoma Cells from Daphniphyllum calycinum

Tang,

Dai,

Lin

et al. 2023

Chin. J. Chem.

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Comprehensive SummaryFive novel Daphniphyllum alkaloids, named dcalycinumines A—E (1—4, 6), and eight previously described Daphniphyllum alkaloids (5, 7—13) were isolated from Daphniphyllum calycinum. Compound 1 is the first Daphniphyllum alkaloid possessing a highly rearranged 6/6/6/7/5/6 hexacyclic architecture with a unique 3‐methyl‐1‐azabicyclo [4,4,0] decane ring system. Compound 2 represents a rare diamino Daphniphyllum alkaloid with an unprecedented 6/5/5/6/6/5 carbon skeleton featuring a unique 1‐aza‐6‐azaspiro [4,5] decane unit, whereas 3 also represents a rare diamino Daphniphyllum alkaloid as a possible precursor of 2. Compound 4 is the second example of C‐22‐nor yuzurimine‐type alkaloids. Their structures and absolute configurations were elucidated by HRESIMS, NMR spectroscopic analyses, ECD calculations, and single‐crystal X‐ray diffraction. Moreover, compound 1 showed remarkable antitumor activities, which could inhibit the proliferation, migration and invasion of nasopharyngeal carcinoma cells, and promoted nasopharyngeal carcinoma cells apoptosis.

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Section: Resultsmentioning

confidence: 99%

Dcalycinumines A—E, Alkaloids with Cytotoxic Activities of Nasopharyngeal Carcinoma Cells from Daphniphyllum calycinum

Tang,

Dai,

Lin

et al. 2023

Chin. J. Chem.

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“…She and co‐workers reported a tetracyclic core 627 of calyciphylline B‐type daphniphyllum alkaloids with the usage of RCM as a pivotal step (Scheme 96). These alkaloids are characterized by pentacyclic scaffold, having a wide range of bioactivities such as anti‐HIV, anticarcinogenic, vasorelaxant, and cytotoxic activities [277] . Their synthetic journey embarked with the allylation of an aldehyde 619 with allylmagnesium bromide followed by acylation with Ac 2 O/DMAP to furnish a diene 620 , which nicely underwent RCM in presence of G‐II catalyst and supplied a cyclohexene derivative 621 in remarkable (90%) yield.…”

Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

“…These alkaloids are characterized by pentacyclic scaffold, having a wide range of bioactivities such as anti-HIV, anticarcinogenic, vasorelaxant, and cytotoxic activities. [277] Their synthetic journey embarked with the allylation of an aldehyde 619 with allylmagnesium bromide followed by acylation with Ac 2 O/DMAP to furnish a diene 620, which nicely underwent RCM in presence of G-II catalyst and supplied a cyclohexene derivative 621 in remarkable (90%) yield. Further, catalytic hydrogenation of 621 with Pd/CÀ H 2 delivered a compound 622.…”

Section: Studies Towards Fragment Syntheses Of Natural Products Based...mentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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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.

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“…According to the literature 15 , to a solution of oCL2 (1.0 equiv.) in THF in an oven dried round bottom flask, TBAF 1.0 M in THF (1.1, 1.2 or 1.5 equiv., respectively) was added dropwise.…”

Section: General Procedures For Optimizing the Deprotection Of Tbdps Groupmentioning

confidence: 99%

A Versatile Synthetic Platform for Discrete Oligo- and Polyesters Based on Optimized Protective Groups Via Iterative Exponential Growth

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Construction of the Tetracyclic Core of Calyciphylline B-Type Daphniphyllum Alkaloids

Cited by 10 publications

References 45 publications

Dcalycinumines A—E, Alkaloids with Cytotoxic Activities of Nasopharyngeal Carcinoma Cells from Daphniphyllum calycinum

Dcalycinumines A—E, Alkaloids with Cytotoxic Activities of Nasopharyngeal Carcinoma Cells from Daphniphyllum calycinum

Metathesis Reactions in Natural Product Fragments and Total Syntheses

A Versatile Synthetic Platform for Discrete Oligo- and Polyesters Based on Optimized Protective Groups Via Iterative Exponential Growth

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