- A formal synthesis of swainsonine by gold-catalyzed allene cyclization
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Image Presented A formal synthesis of swainsonine has been achieved using a highly efficient and diastereoselective gold(III)-catalyzed allene cyclization.
- Bates, Roderick W.,Dewey, Mark R.
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- Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins
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We herein report a direct intermolecular anti-Markovnikov hydroazidation method for unactivated olefins, which is promoted by a catalytic amount of bench-stable benziodoxole at ambient temperature. This method facilitates previously difficult, direct addition of hydrazoic acid across a wide variety of unactivated olefins in both complex molecules and unfunctionalized commodity chemicals. It conveniently fills a synthetic chemistry gap of existing olefin hydroazidation procedures, and thereby provides a valuable tool for azido-group labeling in organic synthesis and chemical biology studies.
- Li, Hongze,Shen, Shou-Jie,Zhu, Cheng-Liang,Xu, Hao
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- ENVIRONMENTALLY-FRIENDLY HYDROAZIDATION OF OLEFINS
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The present invention provides processes for the synthesis of organic azides, intermediates for the production thereof, and compositions related thereto.
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Page/Page column 63; 74-75
(2020/01/24)
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- Anti-Markovnikov Hydroazidation of Alkenes by Visible-Light Photoredox Catalysis
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The anti-Markovnikov hydroazidation of alkenes has been accomplished under visible-light irradiation by using [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 as the photocatalyst and trimethylsilyl azide as the azidating agent. The reactions were greatly facilitated by water, the beneficial effect of which can be attributed to its participation in the reaction as the hydrogen donor, as indicated by deuterium isotope experiments. The reactions proceed under solvent free conditions in the presence of water. 4-Dimethylaminopyridine also exhibited a beneficial effect on the reactions. The present method enabled hydroazidation of several types of unactivated alkenes with good yields and high regioselectivity.
- Wang, Juan-Juan,Yu, Wei
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supporting information
p. 3510 - 3514
(2019/02/19)
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- Dual Photoredox/Copper Catalysis for the Remote C(sp3)?H Functionalization of Alcohols and Alkyl Halides by N-Alkoxypyridinium Salts
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Under mild dual photoredox/copper catalysis, the reaction of N-alkoxypyridinium salts with readily available silyl reagents (TMSN3, TMSCN, TMSNCS) afforded δ-azido, δ-cyano, and δ-thiocyanato alcohols in high yields. The reaction went through a domino process involving alkoxy radical generation, 1,5-hydrogen atom transfer (1,5-HAT) and copper-catalyzed functionalization of the resulting C-centered radical. Conditions for catalytic enantioselective δ-C(sp3)?H cyanation were also documented.
- Bao, Xu,Wang, Qian,Zhu, Jieping
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supporting information
p. 2139 - 2143
(2019/01/25)
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- Novel total synthesis method of 13a-hydroxy tylophorine
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The invention relates to a total synthesis route and method of 13a-hydroxy tylophorine. The method comprises the following steps: synthesizing siloxane nitrile alcohol containing nitrogen from tetrahydrofuran and benzoyl chloride which are simple and easi
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Paragraph 0022
(2018/04/01)
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- Discovery of Macrocyclic Pyrimidines as MerTK-Specific Inhibitors
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Macrocycles have attracted significant attention in drug discovery recently. In fact, a few de novo designed macrocyclic kinase inhibitors are currently in clinical trials with good potency and selectivity for their intended target. In this study, we successfully engaged a structure-based drug design approach to discover macrocyclic pyrimidines as potent Mer tyrosine kinase (MerTK)-specific inhibitors. An enzyme-linked immunosorbent assay (ELISA) in 384-well format was employed to evaluate the inhibitory activity of macrocycles in a cell-based assay assessing tyrosine phosphorylation of MerTK. Through structure–activity relationship (SAR) studies, analogue 11 [UNC2541; (S)-7-amino-N-(4-fluorobenzyl)-8-oxo-2,9,16-triaza-1(2,4)-pyrimidinacyclohexadecaphane-1-carboxamide] was identified as a potent and MerTK-specific inhibitor that exhibits sub-micromolar inhibitory activity in the cell-based ELISA. In addition, an X-ray structure of MerTK protein in complex with 11 was resolved to show that these macrocycles bind in the MerTK ATP pocket.
- McIver, Andrew L.,Zhang, Weihe,Liu, Qingyang,Jiang, Xinpeng,Stashko, Michael A.,Nichols, James,Miley, Michael J.,Norris-Drouin, Jacqueline,Machius, Mischa,DeRyckere, Deborah,Wood, Edgar,Graham, Douglas K.,Earp, H. Shelton,Kireev, Dmitri,Frye, Stephen V.,Wang, Xiaodong
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supporting information
p. 207 - 213
(2017/02/15)
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- The backbone N-(4-azidobutyl) linker for the preparation of peptide chimera
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A robust synthetic strategy for the introduction of the N-(4-azidobutyl) linker into peptides using standard SPPS techniques is described. Based on the example of Cilengitide it is shown that the N-(4-azidobutyl) group exerts similar conformational restra
- Fernandez-Llamazares, Ana I.,Garcia, Jesus,Adan, Jaume,Meunier, David,Mitjans, Francesc,Spengler, Jan,Albericio, Fernando
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supporting information
p. 4572 - 4575
(2013/09/24)
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- Synthesis of new diverse macrocycles from diol precursors
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The formation of a library of diverse macrocycles with different ring sizes from two easily accessible building blocks is presented. Reacting diol precursors with electrophilic reagents lead to 17-membered sulfites and 19-membered malonates in 34-79% yiel
- Madsen, Charlotte M.,Hansen, Martin,Thrane, Marie V.,Clausen, Mads H.
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experimental part
p. 9849 - 9859
(2011/02/22)
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