18498-59-4Relevant articles and documents
Rieke,Cooke
, p. 2674 (1971)
A highly convergent cascade cyclization to cis-hydrindanes with all-carbon quaternary centers and its application in the synthesis of the aglycon of dendronobiloside A
Han, Yejian,Zhu, Lizhi,Gao, Yuan,Lee, Chi-Sing
, p. 588 - 591 (2011)
An efficient and versatile ZnBr2-catalyzed Diels-Alder/ carbocyclization cascade reaction has been developed for construction of highly functionalized cis-hydrindanes (70-96% yields with high diastereoselectivity), and it has been successfully utilized in the synthesis of the aglycon of dendronobiloside A.
In(OTf)3-Catalyzed Cascade Cyclization for Construction of Oxatricyclic Compounds
Bao, Wenli,Tao, Yezi,Cheng, Jiangqun,Huang, Junrong,Cao, Jingming,Zhang, Mengxun,Ye, Weijian,Wang, Bo,Li, Yang,Zhu, Lizhi,Lee, Chi-Sing
, p. 7912 - 7915 (2018)
A highly diastereoselective cascade cyclization reaction has been developed for establishing a series of oxatricyclic compounds using Chan's diene and simple keto alkynal substrates with only 1 mol % of In(OTf)3 as the catalyst in 82-92% yields. The potential utility of this synthetic strategy has been demonstrated in model studies for the construction the core structures of 1α,8α:4α,5α-diepoxy-4,5-dihydroosmitopsin and cortistatin A.
Absolute Configuration of Curacin A, a Novel Antimitotic Agent from the Tropical Marine Cyanobacterium Lyngbya majuscula
Nagle, Dale G.,Geralds, Robin S.,Yoo, Hye-Dong,Gerwick, William H.,Kim, Tae-Seong,et al.
, p. 1189 - 1192 (1995)
Curacin A is a structurally novel antimitotic agent isolated from the Caribbean cyanobacterium Lyngbya majuscula.Its planar structure has been previously determined from a spectroscopic investigation, Here, we define the complete relative and absolute configuration of curacin A by comparison of products obtained from chemical degradation of the natural product with the same substances prepared by synthesis.Curacin A is shown to have 2R, 13R, 19R, 21S absolute configuration.
Synthesis of the furanosteroidal antibiotic viridin.
Anderson, Edward A,Alexanian, Erik J,Sorensen, Erik J
, p. 1998 - 2001 (2004)
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Synthesis of an Alkynyl Methylglyoxal Probe to Investigate Nonenzymatic Histone Glycation
David, Yael,Guber, David,Maksimovic, Igor,Upad, Akhil,Zheng, Qingfei
, (2020)
Methylglyoxal (MGO) is a reactive dicarbonyl metabolite that modifies histones in vivo and induces changes in chromatin structure and function. Here we report the synthesis and application of a chemical probe for investigating MGO-glycation. A two-step synthesis of a Cu-click compatible alkynyl oxoaldehyde probe (AlkMGO) via sequential Dess-Martin and Riley oxidations is presented. This synthesis elevates the accessibility and utility of an important tool for tracking, enriching, and studying MGO-glycation to aid in understanding its underlying biochemical functions.
Divergent and Modular Synthesis of Terpenoid Scaffolds via a AuI Catalyzed One-Pot Cascade
Barriault, Louis,Poyser, Alyson,Revol, Guillaume,Tran, Huy
supporting information, (2021/11/30)
A one-pot cascade sequence to generate synthetically challenging polycyclic scaffolds is reported utilizing a novel Lewis acid gold catalyst for the key cyclization step, enabling the divergent synthesis of both 6,6,5-tricyclic and 6,6,6,5-tetracyclic cores through both ligand and reaction condition control. We have combined the intrinsic complexity and stereoselectivity of cycloadditions with the electronic and steric properties of gold complexes to selectively generate complex polycyclic scaffolds in a single operation.
The Discovery of Two Novel Classes of 5,5-Bicyclic Nucleoside-Derived PRMT5 Inhibitors for the Treatment of Cancer
Quiroz, Ryan V.,Reutershan, Michael H.,Schneider, Sebastian E.,Sloman, David,Lacey, Brian M.,Swalm, Brooke M.,Yeung, Charles S.,Gibeau, Craig,Spellman, Daniel S.,Rankic, Danica A.,Chen, Dapeng,Witter, David,Linn, Doug,Munsell, Erik,Feng, Guo,Xu, Haiyan,Hughes, Jonathan M. E.,Lim, Jongwon,Saurí, Josep,Geddes, Kristin,Wan, Murray,Mansueto, My Sam,Follmer, Nicole E.,Fier, Patrick S.,Siliphaivanh, Phieng,Daublain, Pierre,Palte, Rachel L.,Hayes, Robert P.,Lee, Sandra,Kawamura, Shuhei,Silverman, Steven,Sanyal, Sulagna,Henderson, Timothy J.,Ye, Yingchun,Gao, Yuanwei,Nicholson, Benjamin,Machacek, Michelle R.
, p. 3911 - 3939 (2021/05/04)
Protein arginine methyltransferase 5 (PRMT5) is a type II arginine methyltransferase that catalyzes the post-translational symmetric dimethylation of protein substrates. PRMT5 plays a critical role in regulating biological processes including transcriptio
Iron(III) Nitrate/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Distinguishing between Serial versus Integrated Redox Cooperativity
Mao, Kaining,Nutting, Jordan E.,Stahl, Shannon S.
supporting information, p. 10565 - 10570 (2021/07/28)
Aerobic alcohol oxidations catalyzed by transition metal salts and aminoxyls are prominent examples of cooperative catalysis. Cu/aminoxyl catalysts have been studied previously and feature "integrated cooperativity", in which CuII and the aminoxyl participate together to mediate alcohol oxidation. Here we investigate a complementary Fe/aminoxyl catalyst system and provide evidence for "serial cooperativity", involving a redox cascade wherein the alcohol is oxidized by an in situ-generated oxoammonium species, which is directly detected in the catalytic reaction mixture by cyclic step chronoamperometry. The mechanistic difference between the Cu- and Fe-based catalysts arises from the use iron(III) nitrate, which initiates a NOx-based redox cycle for oxidation of aminoxyl/hydroxylamine to oxoammonium. The different mechanisms for the Cu- and Fe-based catalyst systems are manifested in different alcohol oxidation chemoselectivity and functional group compatibility.
