Article
Chemistry, Organic
Ze-Jun Xu, Xu-Yuan Liu, Ming-Zhu Zhu, Yu-Liang Xu, Yue Yu, Hai-Ruo Xu, Ai-Xia Cheng, Hong-Xiang Lou
Summary: In this study, two types of photoredox-catalyzed cascade reactions using diaryliodonium salts were developed for the concise synthesis of norascyronone A and beta-eudesmol. A rationally designed photoredox-catalyzed arylation/cyclization/Friedel-Crafts cascade reaction was used for the norascyronone synthesis, while a visible-light-induced radical cyclization/acyloxy-migration reaction was explored for the eudesmol synthesis, with mechanistic studies indicating initiation by one-electron oxidation of the enol ester.
Article
Chemistry, Organic
Zhenrong Liu, Zhiqiang Wang, Haiyan Liao, Zheng Li
Summary: An efficient method for constructing 1,2,3-triarylindoles through one-pot multicomponent reactions using calcium carbide, 3mol of iodoarenes, and aromatic amines as starting materials was described. This method allows for the simultaneous formation of five bonds in one step, resulting in a series of target products. The main advantages of this protocol include the use of a convenient alkyne source, a wide scope of substrates, and a simple workup procedure. The method can also be scaled up to gram scale.
Article
Chemistry, Organic
Linghua Zhang, Jie Zhao, Yuqin Jiang, Xinying Zhang, Xuesen Fan
Summary: This paper presents a novel and efficient synthesis method for tetracyclic indenopyrazolopyrazolone derivatives through cascade reactions, demonstrating advantages of accessibility and potential pharmaceutical applications.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Yu-Jiao Wang, Tong-Tong Wang, Cai-Cai Liang, Zi-Hao Li, Li-Ming Zhao
Summary: An efficient synthesis method for indolo[2,1-a]-benzazepinones has been developed through rhodium-catalyzed cascade reactions of 2-arylindoles with allyl alcohols. This work expands the scope of products available through C-H activation/intramolecular annulation reactions of 2-arylindoles in organic synthesis.
Article
Chemistry, Organic
Kelin Wang, Xia Song, Yongdi Xin, Xinying Zhang, Xuesen Fan
Summary: In this study, a condition-controlled selective synthesis of pyranone-tethered indazoles or carbazole derivatives was achieved via cascading reactions of N-nitrosoanilines with iodonium ylides. The formation mechanisms of the products were elucidated, and the developed protocols demonstrated easily controllable selectivity, mild reaction conditions, a clean and sustainable oxidant (air), and structurally diverse valuable products. Furthermore, the utility of the products was showcased by their facile and diverse transformations into synthetically and biologically interesting compounds.
Article
Chemistry, Multidisciplinary
Yu Zhang, Huizhong Liu, Qingshan Shi, Xiaoyang Chen, Xiaobao Xie
Summary: The combination of photocatalysis and biocatalysis has greatly advanced the development of novel synthetic strategies due to functional diversity and stereoselectivity. In this study, a one-pot cascade process combining photo-oxidative fluoridation and bio-reduction was described, which achieved enantiocomplementary vicinal fluoro alcohols with up to 87% isolated yield and 99% ee.
Article
Chemistry, Multidisciplinary
Wei Cao, Zhen Wang, Yan Hao, Tianli Wang, Shaomin Fu, Bo Liu
Summary: We have achieved the total synthesis of sculponin U, a polycyclic C-20-oxygenated kaurane diterpenoid, through a radical cascade cyclization induced by photoinduced electron transfer (PET) of a silyl enolate. Our synthetic strategy involved a Diels-Alder reaction to form the middle six-membered ring and an iron-catalyzed hydrogen atom transfer to close the western cyclohexane ring. The successful preparation of enantiopure silyl enolate as the PET precursor allows for the asymmetric total synthesis of sculponin U and provides a new approach for the synthesis of structurally related compounds and pharmaceutical derivatives.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yuanshuang Xu, Caiyun Yu, Xinying Zhang, Xuesen Fan
Summary: The efficient and unprecedented synthesis of indolyl-tethered spiro[cyclobutane-1,1'-indenes] was achieved through the cascade reaction of 1-(pyridin-2-yl)-1H-indoles with alkynyl cyclobutanols. Mechanistic experiments revealed a sequential process involving alkenylation and intramolecular Friedel-Crafts reaction. This novel protocol demonstrated high substrate scope, chemo- and regioselectivity, removable directing group, and scalability, with the resulting product being easily derivatized further.
Article
Chemistry, Multidisciplinary
Quentin Ronzon, Wei Zhang, Thomas Charote, Nicolas Casaretto, Gilles Frison, Bastien Nay
Summary: This study describes the total synthesis of two fungal cyclotripeptides, (+)-cinereain and (-)-janoxepin, which possess a complex heterocyclic core and exhibit interesting phytotoxic and antimalarial activities. The key step in the synthesis is a one-pot cascade reaction that releases a reactive spiro[2-vinylcyclopropane-1,5'-pyrimidine-4',6'-dione] intermediate through the cyclocondensation of two fragments. This intermediate undergoes a spontaneous retro-Claisen rearrangement, leading to the formation of a 2,5-dihydrooxepin-fused heterocyclic product. The challenging oxepin ring is finally forged through a palladium-catalyzed beta-hydride elimination of an allylic fluoride intermediate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Lilla Koser, Thorsten Bach
Summary: The first total synthesis of (-)-5-deoxyenterocin has been accomplished, starting from pentane-1,3,5-triol with a linear sequence of 16 steps and an overall yield of 0.2%. Key steps of the synthesis include aldol reactions, hydroxylation reactions, and an intramolecular aldol reaction. Despite attempts, a functionalization reaction at position C5 was unsuccessful.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Jiaming Li, Jian Li, Xiaoliang Ji, Runfa He, Yang Liu, Zebin Chen, Yubing Huang, Qiang Liu, Yibiao Li
Summary: This study developed a reversible hydrogen-deuterium exchange reaction for nonactivated olefins, achieving reversible exchange between ordinary olefins and deuterated olefins. By using the lowest cost D2O without precious metal catalysts and ligands, a broad spectrum of functional groups compatibility was achieved.
Article
Chemistry, Organic
Mengjuan Li, Zhiguo Zhang, Nana Ma, Jie Zhao, Hao Wu, Qingfeng Liu, Guisheng Zhang
Summary: A simple and atom-economic one-step protocol is described for the synthesis of biologically valuable 3-isoquinuclidones. The method uses simple starting materials and can be performed under mild conditions, allowing for large-scale synthesis.
Article
Chemistry, Organic
Shengfu Duan, Xing Zhang, Xiangxin Li, Zhiyong Chi, Zhixiang Xie
Summary: The first total synthesis of guajavadimer A, a dimeric caryophyllene-derived meroterpenoid with a unique fused ring system, is reported. The key step in the synthesis involves the construction of the pyrano[4,3,2-de]chromene core via a cascade of double hetero-Diels-Alder reactions. In this approach, a specific compound serves as an effective surrogate for ortho-quinone methide, allowing for efficient and selective synthesis of the target product under mild conditions.
Article
Chemistry, Applied
Weidi Zeng, Linyong Li, Chihao Wang, Duozhi Wang, Lei Zhou
Summary: A relay photocatalytic cascade reaction was developed for the synthesis of 3-amino-1-(difluoromethylidene)tetralins. The reaction utilized readily available starting materials and combined two photoredox catalytic cycles with a single photocatalyst. The method allows for the construction of various 3-amino-tetralins bearing an exo-difluoroethylene unit in good yields.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Qinxuan Wang, Jiun-Le Shih, Ka Yi Tsui, Croix J. Laconsay, Dean J. Tantillo, Jeremy A. May
Summary: This study investigated various types of Huisgen cyclization or nitrene/carbene alkyne cascade reactions with different types of termination. Accessible nitrene precursors were evaluated, and carbonazidates were found to be the only effective initiators. The reaction outcome can be influenced by solvents, terminal alkynyl substituents, and catalysts. The mechanism was studied both computationally (using density functional theory) and experimentally, revealing relevant intermediates and plausible reaction pathways.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
A. F. Fearnley, J. An, M. Jackson, P. Lindovska, R. M. Denton
CHEMICAL COMMUNICATIONS
(2016)
Article
Chemistry, Multidisciplinary
Keith G. Andrews, Declan M. Summers, Liam J. Donnelly, Ross M. Denton
CHEMICAL COMMUNICATIONS
(2016)
Article
Chemistry, Multidisciplinary
J. Saska, W. Lewis, R. S. Paton, R. M. Denton
Article
Multidisciplinary Sciences
Keith G. Andrews, Radmila Faizova, Ross M. Denton
NATURE COMMUNICATIONS
(2017)
Article
Chemistry, Multidisciplinary
Xiaoping Tang, Charlotte Chapman, Matthew Whiting, Ross Denton
CHEMICAL COMMUNICATIONS
(2014)
Review
Chemistry, Organic
Jie An, Ross M. Denton, Tristan H. Lambert, Eric D. Nacsa
ORGANIC & BIOMOLECULAR CHEMISTRY
(2014)
Article
Multidisciplinary Sciences
Rhydian H. Beddoe, Keith G. Andrews, Valentin Magne, James D. Cuthbertson, Jan Saska, Andrew L. Shannon-Little, Stephen E. Shanahan, Helen F. Sneddon, Ross M. Denton
Article
Chemistry, Multidisciplinary
Andrew Jordan, Ross M. Denton, Helen F. Sneddon
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2020)
Article
Chemistry, Multidisciplinary
Emma L. Stoll, Thomas Barber, David J. Hirst, Ross M. Denton
Summary: The study presents a catalytic system for the conversion of carboxylic acids into alcohols, using substoichiometric zinc acetate and N-methyl morpholine in combination with phenylsilane as the nominal terminal reductant. Reaction monitoring by F-19 NMR spectroscopy demonstrates the activation of carboxylic acid and silane through the in situ generation of silyl ester intermediates.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Alessio Calcatelli, Ross M. Denton, Liam T. Ball
Summary: We report a concise and modular approach to synthesizing alpha,alpha-diaryl alpha-amino esters from readily available alpha-keto esters. This method proceeds via ketone umpolung and involves the in situ formation of a Kukhtin-Ramirez intermediate, followed by sequential electrophilic arylation by Bi(V) and SN2 displacement by an amine. It is compatible with a wide range of anilines and primary amines, including derivatives of drugs and proteinogenic amino acids, as well as Bi(V) arylating agents and alpha-keto ester substrates.
Article
Chemistry, Multidisciplinary
Emma L. Stoll, Thomas Tongue, Keith G. Andrews, Damien Valette, David J. Hirst, Ross M. Denton
Article
Chemistry, Multidisciplinary
Rhydian H. Beddoe, Daniel C. Edwards, Louis Goodman, Helen F. Sneddon, Ross M. Denton
CHEMICAL COMMUNICATIONS
(2020)
Meeting Abstract
Chemistry, Multidisciplinary
Rhydian Beddoe, Helen Sneddon, Ross Denton
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Multidisciplinary
Keith G. Andrews, Ross M. Denton
CHEMICAL COMMUNICATIONS
(2017)
Review
Chemistry, Organic
Rhydian H. Beddoe, Helen F. Sneddon, Ross M. Denton
ORGANIC & BIOMOLECULAR CHEMISTRY
(2018)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.