Review
Chemistry, Multidisciplinary
Zhen Yang
Summary: The total synthesis endeavors contribute to the discovery and invention of new synthetic reactions to advance organic synthesis. Bioactive compounds share common features, such as molecular complexity, protein-binding ability, structural rigidity, and three-dimensionality. Total synthesis offers an alternative solution for generating scarce natural products and their derivatives for studying their biological functions.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Lisa-Catherine Rosenbaum, Maximilian Haefner, Tanja Gaich
Summary: A racemic and scalable enantioselective total synthesis of (+)-waihoensene was achieved, featuring an angular triquinane substructure with an all-cis-fused tetracyclic backbone and six contiguous stereocenters, four of which are quaternary. Enantioselectivity was introduced at an early stage, and key structural features were efficiently installed through several diastereoselective reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Hui Wang, Yi Liu, Hongyuan Zhang, Baochao Yang, Haibing He, Shuanhu Gao
Summary: The asymmetric total syntheses of cephalotaxus C19 diterpenoids, which possess a unique cycloheptene A ring with a chiralmethyl group at C-12, were achieved using a universal strategy. Six members, including previously unreported compounds, were successfully synthesized. The concise approach involved a Nicholas/Hosomi-Sakurai cascade reaction to generate the cycloheptene ring with a chiral methyl group, followed by an intramolecular Pauson-Khand reaction for the construction of the target molecules' complete skeleton. This work provides a new strategy for the synthetic analysis of cephalotaxus diterpenoids and structurally related natural products.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Tianhao Ma, Hao Cheng, Mallesham Pitchakuntla, Weihao Ma, Yanxing Jia
Summary: We have achieved the first total synthesis of (-)-principinol C, which is a natural product with an intriguing and complex 5/7/6/5 tetracyclic skeleton and eight contiguous stereocenters. The key step in assembling the 5/7/6/5 tetracyclic skeleton was the intramolecular Pauson-Khand reaction. This synthetic route represents the first application of intramolecular Pauson-Khand reaction of enyne to construct the 7,5-bicyclic ring system in natural product synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Anding Li, Ziru He, Bingyan Liu, Zhen Yang, Zichun Zhang
Summary: In this study, a concise and stereoselective total synthesis of (+/-)-cephanolide B was accomplished in 15 steps. The key steps in the synthesis included an intermolecular Diels-Alder reaction, a tandem reaction featuring intramolecular Pauson-Khand reaction, 6 pi-electrocyclization, and oxidative aromatization to construct the ABC-tricyclic rings (6-5-6), as well as a phthaloyl peroxide-mediated arene oxygenation to install the C-13 phenol group.
Article
Chemistry, Multidisciplinary
Ridge Michael P. Ylagan, Eric Jaewon Lee, Daniela E. Negru, Paolo Ricci, Bohyun Park, Haram Ryu, Mu-Hyun Baik, P. Andrew Evans
Summary: We report an enantioselective rhodium(I)-catalyzed Pauson-Khand reaction using 1,6-chloroenynes that contain challenging 1,1-disubstituted olefins. Unlike previous studies, this new approach allows for a wider range of substrates, including both carbon and heteroatom tethers with polar and non-polar substituents on the alkene. DFT calculations reveal the critical role of the halide, which pre-polarizes the alkyne and provides the appropriate steric profile for a favorable interaction with the chiral diphosphine ligand.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yun-Peng Zou, Zheng-Lin Lai, Meng-Wei Zhang, Jianzhao Peng, Shuai Ning, Chuang-Chuang Li
Summary: The first total synthesis of (+/-)- and (-)-daphnilloninB, a daphnicyclidin-type alkaloid with a novel hexa-cyclic core, was achieved through a series of chemical reactions. The B/C/D ring system was efficiently constructed using a mild intramolecular cycloaddition and a GrubbsII catalyst-catalyzed radical cyclization. The E/F fused ring system was synthesized via a diastereo-selective intramolecular Pauson-Khand reaction. The challenging hexa-cyclic core was reassembled from a hexa-cyclic framework found in calyciphylline A-type Daphniphyllum alkaloids through a unique Wagner-Meerwein rearrangement.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Charles J. Dooley, Scott D. Rychnovsky
Summary: The first total synthesis of a norsesquiterpene derived from the Illicium genus is reported. This natural product displays neurotrophic properties and has potential as a therapeutic for neurodegenerative diseases.
Article
Chemistry, Applied
Joan Salto, Maria Biosca, Oscar Pamies, Montserrat Dieguez
Summary: A set of complex tricyclic compounds containing multiple functional groups and stereogenic centers has been synthesized in only two steps with excellent diastereo- and enantioselectivities, using a highly versatile and enantioselective Pd-catalyzed reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Zhenyu Zhang, Wei Zhang, Jun-Chen Tang, Jin-Teng Che, Zhongchao Zhang, Jia-Hua Chen, Zhen Yang
Summary: The researchers synthesized (+)-Haperforin G in 20 steps from commercially available starting materials. They used a Co-catalyzed intramolecular Pauson-Khand reaction to selectively construct a cyclopentanone with an all-carbon quaternary stereogenic center at the bridge-head position. Light-initiated photocatalysis was employed for the convergent and asymmetric cross-coupling of the unstabilized C(sp(3)) radical with an enone. This developed chemistry opens up possibilities for synthesizing structurally diverse analogs of haperforin G (6).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xin-Ting Liang, Bao-Chuan Sun, Chang Liu, Yuan-He Li, Nan Zhang, Qian-Qian Xu, Zhong-Chao Zhang, Yi-Xin Han, Jia-Hua Chen, Zhen Yang
Summary: A concise and diastereoselective method has been developed for the construction of the key ring system of spirochensilide A, paving the way for the first asymmetric total synthesis of (-)-spirochensilide A.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Dong Whan Jee, Hee-Yoon Lee
Summary: The structural identity of pethybrene was confirmed to be the theoretically proposed 6-5-5 tricyclic structure through total syntheses of two putative structures. Structure 1 was synthesized in 13 steps via Intramolecular Pauson-Khand reaction, while the new proposed structure 2 was obtained from a known [2+2] cycloaddition product in 3 steps.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Ding Ma, Naifeng Hu, Junli Ao, Shaoli Zang, Guo Yu, Guangxin Liang
Summary: Pauson-Khand reactions with concomitant C-O bond cleavage have been developed for constructing complex bicyclic ring systems with precise control over regio- and stereochemistry. The mechanism behind this reaction has been proposed based on deuterium labelling experiments.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Paul Shaw, Storm J. Hassell-Hart, Gayle E. Douglas, Andrew G. Malcolm, Alan R. Kennedy, Gemma White, Laura C. Paterson, William J. Kerr
Summary: In this study, we applied silyl enol ether moieties as efficient alkene coupling partners within cobalt-mediated intramolecular Pauson-Khand reactions. This cyclization strategy delivers valuable oxygenated cyclopentenone products in high yields and allows for the incorporation of a variety of decorated structures.
Article
Chemistry, Multidisciplinary
Haoran Dong, Dachao Hu, Benke Hong, Jin Wang, Xiaoguang Lei
Summary: The first total syntheses of four natural antibiotics, vermisporin, PF1052/AB4015-A, AB4015-L, AB4015-B, and one hydrogenated natural product derivative, AB4015-A2, featuring a tetramic acid bearing cis-decalin ring, are reported. The functionalized cis-decalin ring was constructed via a diastereoselective intramolecular Diels-Alder (IMDA) reaction, with a rare endo-boat transition state. The efficient installation of the sterically hindered epoxy group in vermisporin, PF1052/AB4015-A, and AB4015-L was achieved through an intramolecular neighboring-group-oriented strategy, and the desired tetramic acid structure was obtained through a one-pot aminolysis/Dieckmann condensation cascade using L-amino acid derivatives. The total synthesis allowed for the unequivocal verification of the absolute configuration of these natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Qian Wu, Yubo Cui, Guifeng Xia, Jinlong Yang, Shuming Du, Xinhong Xiong, Li Yang, Dong Xu, Xu Deng, Jiaxi Cui
Summary: Passive daytime radiative cooling (PDRC) technology, while promising for global spacing cooling, faces limitations in practical application due to reduced cooling effectiveness caused by wear and dirt contamination. Researchers have developed a renewable armor structure using fluorinated hollow glass microspheres to enhance the anti-fouling and cooling properties of PDRC coatings. The coatings exhibit high solar reflectance and thermal emittance, leading to significant temperature reduction below ambient temperature.
CHINESE CHEMICAL LETTERS
(2024)
Article
Chemistry, Multidisciplinary
Qiang Bei, Bei Zhang, Kaifeng Wang, Shiming Zhang, Guichuan Xing, Clement Cabanetos
Summary: The power conversion efficiency (PCE) of organic solar cells (OSCs) has reached 20% in recent years, thanks to the advantages of organic photoactive materials. Benzothiadiazole (BT) has attracted significant research attention as a building block of OSCs. OSCs based on BT structure have shown diversity, and the increasing PCE values indicate a promising future for OSCs. This review analyzes the progress made in the last decades, focusing on effective BT small-molecules and BT polymers for OSCs. The structure-property relationships, donor-acceptor matching criteria, and morphology control approaches are discussed. The remaining challenges and a personal perspective on the future advancement of OSCs are summarized.
CHINESE CHEMICAL LETTERS
(2024)
Article
Chemistry, Multidisciplinary
Rong He, Dandan Tang, Ningge Xu, Heng Liu, Kun Dou, Xuejun Zhou, Fabiao Yu
Summary: Nasopharyngeal carcinoma (NPC) is a common malignant tumor of the head and neck, with a high incidence in China and Southeast Asian countries. In this study, a novel near-infrared fluorescent probe, SNAFL-GSH, was designed and synthesized for the detection of glutathione (GSH). The probe showed selective detection of GSH and the ability to distinguish normal and cancer cells. It has great potential for application in the diagnosis and evaluation of NPC.
CHINESE CHEMICAL LETTERS
(2024)
Article
Chemistry, Multidisciplinary
Zhukang Guo, Baijiang Jin, Yile Fang, Lian Jin, Song Li, Yan Deng, Zhu Chen, Hui Chen, Yuanying Zhang, Rabia Usman, Nongyue He
Summary: This study isolated primary cells that can be stably passaged from spontaneous tumors of genetically engineered pancreatic ductal adenocarcinoma model mice and used an autonomously developed automated screening instrument for efficient nucleic acid aptamer screening. The obtained aptamers were affinity verified at the cellular level. The study also investigated the impact of cell growth environment difference on the recognition ability of aptamers and confirmed the targeting ability and drug loading ability of the aptamer.
CHINESE CHEMICAL LETTERS
(2024)
Article
Chemistry, Multidisciplinary
Zhongshan Yang, Qiqi Zhang, Hui Song, Xin Chen, Jiwei Cui, Yanhui Sun, Lequan Liu, Jinhua Ye
Summary: Methane chemistry is a significant area of research in catalysis. Converting methane into value-added chemicals is desirable but challenging due to its high C-H bonding energy and lack of pi bonding or unpaired electrons. Photocatalytic partial oxidation of methane to liquid oxygenates is a promising technology for achieving high efficiency and selectivity under mild conditions. The choice and activation of oxidants are crucial for its performance.
CHINESE CHEMICAL LETTERS
(2024)
Article
Chemistry, Multidisciplinary
Peng Shan, Jing Liao, Jiayi Li, Chengyan Wang, Jie Zhou, Linqiang Mei, Yunlu Dai, Qiang Wang, Wenyan Yin
Summary: This study reports an oral radioprotectant Gel@GYY that combines a gelatin-based hydrogel and a pH-responsive hydrogen sulfide donor. Gel@GYY has excellent adhesion and sustained release properties, allowing it to release H2S in the gastrointestinal tract and effectively scavenge free radicals induced by radiation. It also reduces inflammation and has biodegradable properties.
CHINESE CHEMICAL LETTERS
(2024)
Article
Chemistry, Multidisciplinary
Lu Liu, Ziyi Liu, Jingnan Cui, Guiling Ning, Weitao Gong
Summary: The development of new metal-free heterogeneous catalysts has been the subject of extensive research. In this study, a new Troger's base (TB)-derived porous organic polymer (POPs) was designed and prepared by integrating multifunctional monomers. The resulting polymer, which combines the advantages of pillar[5]arene macrocycle and TB moiety, exhibited enhanced catalytic performance in Knoevenagel condensation and CO2 conversion, serving as an effective metal-free catalyst. This work provides a new strategy for fabricating metal-free heterogeneous catalysts based on macrocyclic POPs.
CHINESE CHEMICAL LETTERS
(2024)
Article
Chemistry, Multidisciplinary
Leyong Zhou, Changyin Yang, Weitao Dou, Tongxia Jin, Haibo Yang, Lin Xu
Summary: This review summarizes the application of micro/nanofluidic techniques in constructing supramolecular assemblies of different scales, and highlights the advantages of these techniques over conventional synthesis methods. Furthermore, it emphasizes the potential of micro/nanofluidic systems in improving our understanding of supramolecular self-assembly processes.
CHINESE CHEMICAL LETTERS
(2024)
Article
Chemistry, Multidisciplinary
Yanchao Jin, Suixiaochen Chen, Peiwen Huang, Xiongjian Chen, Chun-Yan Lin, Li-Ping Li, Xiao Chen, Rui Ding, Jianxi Liu, Riyao Chen
Summary: In this study, magnesium and coconut shell carbon were used to disinfect water by adsorbing copper(II) and converting dissolved oxygen to hydrogen peroxide through Mg corrosion. The copper was enriched on the carbon surface and efficiently catalyzed the hydrogen peroxide to inactivate E.coli. The process showed promising disinfection performance both in laboratory experiments and real wastewater treatment.
CHINESE CHEMICAL LETTERS
(2024)
Article
Chemistry, Multidisciplinary
Haihong Lai, Zehong Chen, Hao Zhuo, Yijie Hu, Xuan Zhao, Jiwang Yi, Hongzhi Zheng, Ge Shi, Yifan Tong, Ling Meng, Xinwen Peng, Linxin Zhong
Summary: By altering the pyrolysis route of cellulose nanofiber, the structural defects of carbon aerogels can be reduced, leading to improved compressibility and stress retention, as well as higher stress sensor sensitivity and temperature coefficient.
CHINESE CHEMICAL LETTERS
(2024)
Article
Chemistry, Multidisciplinary
Lina Guo, Jinsong Ding, Wenhu Zhou
Summary: Bacteria-based tumor therapy has resurfaced due to the revolution of tumor immunotherapy, offering unique solutions for traditional tumor treatments. Bacteria with active tropism can selectively colonize tumor sites and suppress tumor growth through various mechanisms, making them attractive tools for tumor treatment. This critical review introduces recent advances in bacteria-based tumor therapy, including bacterial properties, their benefits for tumor therapy, anti-tumor mechanisms, challenges, and future perspectives.
CHINESE CHEMICAL LETTERS
(2024)
Article
Chemistry, Multidisciplinary
Lan Liang, Chuanbin Wang, Xukai Lu, Yunan Sun, Beibei Yan, Ning Li, Guanyi Chen, Li'an Hou
Summary: This study investigates the interactions between phenol and benzaldehyde in the ECH process through experiments and theoretical calculations. The results show that phenol can accelerate the conversion of benzaldehyde, while benzaldehyde inhibits the conversion of phenol. The research provides a theoretical basis for the application of ECH in practical bio-oil upgrading.
CHINESE CHEMICAL LETTERS
(2024)
Article
Chemistry, Multidisciplinary
Pengcheng Fan, Yuhao He, Junan Pan, Ning Sun, Qiyu Zhang, Chen Gu, Kang Chen, Weinan Yin, Longlu Wang
Summary: This study focuses on the recent progress in hydrogen evolution reaction (HER) based on photothermal effect. It introduces the main pathways of photothermal conversions applied in H2 evolution, summarizes the functions of the photothermal effect, and presents a method to improve the catalytic system through thermal means. The study also discusses the challenges and outlook in this promising area.
CHINESE CHEMICAL LETTERS
(2024)
Article
Chemistry, Multidisciplinary
Leiduo Lai, Hongyu Zhou, Yichen Hong, Mengfan Luo, Yang Shi, Heng Zhang, Zhaokun Xiong, Gang Yao, Bo Lai
Summary: In this study, a facile ammonia reduction strategy was proposed and a novel FeVO3-x catalyst was synthesized for the activation of peroxymonosulfate (PMS) to degrade the pharmaceutical carbamazepine (CBZ). The results showed that the system could rapidly degrade CBZ and generate various active species involved in the degradation process.
CHINESE CHEMICAL LETTERS
(2024)
Article
Chemistry, Multidisciplinary
Tangxin Xiao, Xiuxiu Li, Liangliang Zhang, Kai Diao, Zheng-Yi Li, Xiao-Qiang Sun, Leyong Wang
Summary: This study presents the construction of a supramolecular light harvesting system based on sequential energy transfer. The system demonstrates tunable fluorescence emission through self-assembly of polymers into nanoparticles, achieving efficient two-step light harvesting.
CHINESE CHEMICAL LETTERS
(2024)