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Goniothalamin是由番荔枝科(annonaceae)家族中分离出的抗肿瘤活性天然产物分子,具有苯乙烯基及α,β-不饱和-δ-内酯两个关键片段。药物化学家近年来利用氟原子或者含氟基团对这两个关键药效基团进行了系统的结构修饰,试图利用氟独特的物理化学性质调控药效基团电子属性以获取具有更佳生理活性的化合物。本文主要从含氟基团引入的位点设计以及合成方法角度,总结了goniothalamin内酯含氟修饰物合成与生理活性研究进展,并进行了发展前景展望。 相似文献
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萜类化合物在自然界中广泛存在,其中倍半萜内酯广泛存在于各种药用植物中,是许多传统中草药的主要活性成分,然而这类化合物的化学全合成却极具挑战性.山道年是一种廉价的可再生资源,且光促进的山道年重排反应是一种构建愈创木内酯骨架的高效方法,在萜类天然产物合成中得到广泛应用.就光促进的山道年重排在复杂萜类天然产物的合成工作进行简单的概述,主要包括倍半萜内酯及其寡聚物全合成以及个别二萜天然产物的骨架合成研究. 相似文献
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含氟β-氨基酸及其衍生物具有特殊的生理活性, 其合成方法的研究近年来受到广泛关注. 以直接氟化法和间接氟化法分类, 概述了含氟β-氨基酸及其衍生物的合成方法及最新研究进展, 对一些已知化合物的生理活性及药用价值作了初步归纳. 相似文献
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含氟杂环化合物由于其优异的物理化学性质,在有机化学、药物化学、材料科学等诸多领域扮演着重要的角色.但自然界中,天然含氟杂环化合物屈指可数,开发高效的含氟杂环化合物的合成方法显得尤为重要.随着过渡金属催化、光催化以及电催化自由基反应的迅速发展,自由基化学在合成领域取得了突破性进展,激发了有机化学家利用自由基化学构建含氟杂环的兴趣.主要以不饱和烃的单氟烷基化、二氟烷基化、三氟甲基化、三氟烷氧/硫/硒基化、全氟烷基化以及杂环的直接C—H氟烷基化进行分类,从过渡金属催化、光催化以及电催化等几个方面,对自由基介导的含氟侧链杂环化合物的构建进行讨论. 相似文献
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Stereodivergent and Protecting‐Group‐Free Synthesis of the Helicascolide Family: A Rhodium‐Catalyzed Atom‐Economical Lactonization Strategy
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Alexander M. Haydl Dino Berthold Pierre A. Spreider Prof. Dr. Bernhard Breit 《Angewandte Chemie (International ed. in English)》2016,55(19):5765-5769
Natural products of polyketide origin, in particular small‐sized lactones often possess a very broad range of impressive biological activities. An efficient way to demonstrate the concise access to six‐membered lactones was emphasized as part of a stereodivergent and protecting‐group‐free synthesis of all three representatives of the helicascolide family. This strategy features an atom‐economical and highly diastereoselective rhodium‐catalyzed “head‐to‐tail” lactonization by an intramolecular addition of ω‐allenyl‐substituted carboxylic acids to terminal allenes, including the selective construction of a new stereocenter in the newly formed core structures. The excellent selectivities with which the helicascolide precursors were obtained are remarkable, thus resulting in an expeditious and highly efficient natural product synthesis. 相似文献
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Satoshi Motodate Takuya Kobayashi Mikio Fujii Prof. Tomoyuki Mochida Dr. Taichi Kusakabe Shigeki Katoh Prof. Hiroyuki Akita Prof. Keisuke Kato 《化学:亚洲杂志》2010,5(10):2221-2230
Bis(oxazoline)‐palladium(II) catalyzed carbonylation of homopropargyl alcohols afforded acyclic methoxyacrylate 2 and 6‐membered lactone 3a , 3b , 3d , 3e , 3f , 3g , 3h , 3i , 3j , 3k in good combined yield. In the case of propargyl alcohols, 5‐membered lactones 3p , 3q , 16 were obtained in moderate yields. The one‐pot synthesis of kawa lactones 3a , 3r , 3s and formal synthesis of dihydroxycystothiazole A and dihydroxycystothiazole C are presented. To elucidate the stereochemistry of (+)‐annularin G and (?)‐annularin H, the first asymmetric syntheses of these natural products were achieved. 相似文献
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Paulo H.S. PaiotiFernando Coelho 《Tetrahedron letters》2011,52(46):6180-6184
We disclosed herein a diastereoselective approach for the total syntheses of (±)-Leiocarpin A and (±)-Goniodiol. These biologically active styryl lactones were obtained from a common intermediate, prepared in five steps and 40% overall yield, using a simple synthetic sequence starting from a Morita-Baylis-Hillman adduct. The total syntheses of these styryl lactones were accomplished in nine steps. This is the first report on the total synthesis of this class of natural products starting from Morita-Baylis-Hillman adduct. 相似文献
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Stereoselective synthesis of the fully protected 18-membered macrocyclic lactones as the immediate precursors of the natural products, sorangiolides A and B, is described. The key steps used in the synthesis include the sp3-hybridized carbon-carbon Fu cross coupling, the stereoselective Evans' aldol reaction with 1,5-anti induction, the 1,3-diastereoselective syn reduction of a beta-hydroxyketone intermediate, and Mukaiyama macrolactonization reactions. 相似文献
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Arylnaphthalene lactones are natural products which can be isolated from a wide range of plants and have the significant biological activities including cytotoxicity, antimicrobial, diuretic, and ion channel blocking. The drawback of the previous intramolecular Diels–Alder reaction of 3-arylprop-2-ynyl 3-arylpropiolates was to generate two regioisomers of arylnaphthalene lactone without selectivity. Herein, we report a convenient and regioselective synthesis method in which the intramolecular Diels–Alder reaction of an arylalkene–arylalkyne and subsequent DDQ oxidation was used for Type I and Type II arylnaphthalene lactones, respectively. We demonstrated the synthesis of three lignans, taiwanin C (Type I), justicidin E (Type II), and daurinol (Type I and anti-cancer activity). 相似文献
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Dr. Govind Goroba Pawar Dr. Ajit Prabhakar Kale Pooja Sah Prof. Manmohan Kapur 《European journal of organic chemistry》2023,26(3):e202201277
The total synthesis of the 14-membered resorcylic acid lactone neocosmosin A is described. The key step in the synthesis is the palladium-catalyzed α-arylation of TES-enol ethers of enones. The employment of the α-arylation approach to this class of resorcylic acid lactones is a new approach, which has the scope of being generalized into a unified approach for the synthesis of this class of natural products. 相似文献
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[reaction: see text] The first enantiospecific, regiospecific total synthesis of the enantiomers of N(a)-methylpericyclivine and N(a)-methylakuammidine as well as the ring-A oxygenated natural products (+)-10-methoxy N(a)-methylpericyclivine and 10-hydroxy N(a)-methylpericyclivine was achieved. The lactones (see 19, 22, and 25) are key to the formation of the beta-axial methyl ester moiety. 相似文献
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Arylnaphthalene lignan lactones are valuable natural products with promising anticancer and antiviral properties. In an effort to simplify their synthesis, we investigated a one-pot multicomponent coupling reaction between phenylacetylene, carbon dioxide, and 3-bromo-1-phenyl-1-propyne. After the corresponding 1,6-diyne was generated in situ, cyclization afforded the desired product. The level of regioselectivity was enhanced through the tuning of electronic properties. The use of cinnamyl bromide which led to the formation of a 1,6-enyne intermediate was also studied. 相似文献
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Guanghao Huang Prof. Cyrille Kouklovsky Dr. Aurélien de la Torre 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(15):4760-4788
Inverse-electron-demand Diels–Alder (IEDDA) reactions of electron-poor 2-pyrones as electrophilic dienes have been extensively studied in the past fifty years. These reactions provide an efficient access to bridged bicyclic lactones and their derivatives, such as densely functionalized 1,3-cyclohexadienes after CO2 extrusion and polysubstituted aromatic compounds through elimination. This reaction has been used for the synthesis of many biologically active natural products and drug candidates. In this review, the developments of these IEDDA reactions including non-catalytic, Lewis acid-catalyzed and organocatalytic IEDDA reactions, and their applications in total synthesis are discussed in detail. 相似文献