Withanolide A: synthesis and structural requirements for neurite outgrowth?
Chemical Science Pub Date: 2013-04-23 DOI: 10.1039/C3SC50653C
Abstract
The exploration of different routes leading to the stereoselective synthesis of the neuritogenic steroid withanolide A is reported in full detail. Notable features of the synthesis include a Corey–Seebach homologation, a vinylogous aldol reaction, a singlet oxygen Schenck-ene reaction, and finally, a late-stage Wharton transposition. Semi-synthetic elaboration of the natural product resulted in 15 derivatives allowing a better understanding of its inherent reactivity pattern as well as its biological properties related to neuronal differentiation and neurite outgrowth.
Recommended Literature
- [1] Enantio- & chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330 Sowmyalakshmi VenkataramanRSC Adv., 2015,5, 73807-73813 10.1039/C5RA13593A
- [2] Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials? Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-GarayoaRSC Adv., 2017,7, 24133-24139 10.1039/C7RA03845C
- [3] Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications? Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping XieNanoscale Adv., 2020,2, 3921-3932 10.1039/D0NA00381F
- [4] Evolution of shape, size, and areal density of a single plane of Si nanocrystals embedded in SiO2 matrix studied by atom probe tomography Bin Han,Yasuo Shimizu,Gabriele Seguini,Celia Castro,Gérard Ben Assayag,Koji Inoue,Yasuyoshi Nagai,Sylvie Schamm-Chardon,Michele PeregoRSC Adv., 2016,6, 3617-3622 10.1039/C5RA26710B
- [5] Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study? Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander OrlovCatal. Sci. Technol., 2015,5, 2059-2064 10.1039/C4CY01563K
- [6] Excited state dynamics of symmetric and asymmetric Cr3(dpa)4Cl2 measured using femtosecond transient absorption spectroscopy? Chao-Han Cheng,Wen-Zhen Wang,Shie-Ming Peng,I-Chia ChenPhys. Chem. Chem. Phys., 2017,19, 25471-25477 10.1039/C7CP03968A
- [7] Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings Analyst, 1996,121, 785-788 10.1039/AN9962100785
- [8] Evolution study of photo-synthesized gold nanoparticles by spectral deconvolution model: a quantitative approach Chung-Sung Yang,Mong-Shian Shih,Fang-Yi ChangNew J. Chem., 2006,30, 729-735 10.1039/B516465F
- [9] Exchanged ligands on the surface of a giant cluster: [(MoO3)176(H2O)63(CH3OH)17Hn](32 – n)– Chem. Commun., 1998, 1501-1502 10.1039/A801804I
- [10] Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries? Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde WangJ. Mater. Chem. A, 2018,6, 516-526 10.1039/C7TA08423D
Journal Name：Chemical Science
research_products
-
CAS no.: 89640-58-4
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)