An efficient and convenient formal synthesis of Jaspine B from d-xylose

Zhao, Mingli; Zhang, En; Gao, Jie; Zhang, Zhao; Zhao, Yutao; Qu, Wen Tao; Liu, Hong‐Min

doi:10.1016/j.carres.2012.01.013

Cited by 19 publications

(5 citation statements)

References 47 publications

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“…1.1 化合物的合成通过文献调研, 原料 6 [24] 与二级胺在三乙酰氧基硼氢化钠的作用下发生还原胺化反应生成化合物 7, 化合物 7 在氢气条件下钯碳还原叠氮并脱去苄基得到化合物 8 (Scheme 1). 其中化合物 8f 在进行钯碳氢化反应时, 1,2,3,4-四氢异喹啉开环得到 2-甲基苯乙胺.…”

Section: 结果与讨论unclassified

“…我们课题组已经设计完成了一条以 D-木糖为原料全合成 Jaspine B 的路线 [24] , 并且设计合成了一系列含有三唑的 Jaspine B 类似物 5 [25] . 由于含氮杂环化合物和 H 2 S 供体重要的生物活性, 为了发现更好活性的 Jaspine B 类似物, 本文设计并合成了一系列 3-epi-Jaspine B 类似物, 并对其进行生物活性评价.…”

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Synthesis and Antitumor Evaluation of 3-epi-Jaspine B Analogues

张恩¹,

王上²,

焦伟伟³

et al. 2017

Chin. J. Org. Chem.

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Jaspine B is a natural product with significant antitumor activity, which was isolated from the marine sponge Pachastrissa sp. In order to find new antitumor compounds with high efficiency and succinct synthetic methods, a series of 3-epi-jaspine B analogues were designed and synthesized. 16 compounds were synthesized and all of them were unknown in the literature. Their structures were determined by 1 H NMR, 13 C NMR and HRMS. The antitumor activity of these compounds against four tumor cell lines B16-F10, A-549, MCF-7 and PC-3 was assayed using thiazolyl blue (MTT) assay, and some compounds showed potent inhibitory effect on tumor cells. Compounds 8f and 11 were more potent against A-549 with IC 50 of (9.646±0.984) and (7.144±0.854) μg/mL.

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Section: 结果与讨论unclassified

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Synthesis and Antitumor Evaluation of 3-epi-Jaspine B Analogues

张恩¹,

王上²,

焦伟伟³

et al. 2017

Chin. J. Org. Chem.

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“…It was also reported that pachastrissamine and its stereoisomers inhibit sphingosine kinases (SphKs) and atypical protein kinase C [ 5 ]. Because of its intriguing biological activity, it has been an interesting target for synthetic chemists, and various synthetic routes to pachastrissamine have been reported [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 ]. However, the structure-activity relationship (SAR) of pachastrissamine remains relatively unreported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Carbocyclic Analogues of Pachastrissamine

et al. 2015

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A series of carbocyclic analogues of naturally-occurring marine sphingolipid pachastrissamine were prepared and biologically evaluated. The analogues were efficiently synthesized via a tandem enyne/diene-ene metathesis reaction as a key step. We found that the analogue 4b exhibited comparable cytotoxicity and more potent inhibitory activity against sphingosine kinases, compared to pachastrissamine. Molecular modeling studies were conducted to provide more detailed insight into the binding mode of 4b in sphingosine kinase. In our docking model, pachastrissamine and 4b were able to effectively bind to the binding pocket of sphingosine kinase 1 as co-crystalized sphingosine. However, 4b showed a hydrophobic interaction with Phe192, which suggests that it contributes to its increased inhibitory activity against sphingosine kinase 1.

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“…L-serine [7–18], or by asymmetric catalysis [19–25]. Several publications also focused on the synthesis of stereoisomers of the natural product [4,12,16–17 19,26–28] because these compounds also showed comparable biological activities [4–5]. …”

Section: Introductionmentioning

confidence: 99%

Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C₃-building block

Schmiedel¹,

Stefani²,

Reißig³

2013

Beilstein J. Org. Chem.

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SummaryHerein we present the synthesis of the anhydrophytosphingosine jaspine B and three of its stereoisomers using a carbohydrate-derived alkoxyallene in order to obtain the products in enantiopure form. Key step of the reaction sequence is the addition of the lithiated alkoxyallene to pentadecanal, setting the configuration at the later C-2 of the ring system. This reaction step proceeds with moderate selectivity and therefore leads to a stereodivergent approach to the natural product and its enantiomer. The gold-catalyzed 5-endo-cyclization affords the corresponding dihydrofurans, which after separation, azidation of the enol ether moiety and two subsequent reduction steps give the natural product and its stereoisomers.

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An efficient and convenient formal synthesis of Jaspine B from d-xylose

Cited by 19 publications

References 47 publications

Synthesis and Antitumor Evaluation of 3-epi-Jaspine B Analogues

Synthesis and Antitumor Evaluation of 3-epi-Jaspine B Analogues

Synthesis and Biological Evaluation of Carbocyclic Analogues of Pachastrissamine

Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C₃-building block

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An efficient and convenient formal synthesis of Jaspine B from d-xylose

Cited by 19 publications

References 47 publications

Synthesis and Antitumor Evaluation of 3-epi-Jaspine B Analogues

Synthesis and Antitumor Evaluation of 3-epi-Jaspine B Analogues

Synthesis and Biological Evaluation of Carbocyclic Analogues of Pachastrissamine

Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C3-building block

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Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C₃-building block