Article
Biochemistry & Molecular Biology
Yogesh Yadav, Rajdeep Tyagi, Kanchan Yadav, Ghanshyam Tiwari, Ram Sagar
Summary: The Ferrier rearrangement using SnCl4 as catalyst allows for the synthesis of 2,3-unsaturated glycopyranosides with high stereoselectivity starting from the hydroxyl group at the C-3 position. This method has several advantages, including strong anomeric selectivity, high yields, and short reaction time.
CARBOHYDRATE RESEARCH
(2023)
Article
Chemistry, Physical
Nan Jiang, Yuling Mei, Yu Yang, Youxian Dong, Zekun Ding, Jianbo Zhang
Summary: A two-step methodology was developed for the synthesis of chiral pyrroles from 2-nitroglycals via Ferrier rearrangement and Barton-Zard reaction without transition metal catalysts. The highly stereoselective synthesis of diverse 2-nitro-2,3-unsaturated glycosides in excellent yields was achieved using N-heterocyclic carbene (NHC) catalyst and K2CO3. Successful demonstration of gram-scale synthesis of one chiral pyrrole was shown using a one-pot strategy.
Article
Biochemistry & Molecular Biology
Tao Xiong, Rui Xie, Cai Huang, Xin Lan, Nianyu Huang, Hui Yao
Summary: This review summarizes the synthetic methods of thiosugars using glycal donors based on promoters/catalysts, including main-group, transition metal, rare-earth, and solid-supported catalysts.
JOURNAL OF CARBOHYDRATE CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Miran Lemmerer, Nuno Maulide
Summary: The combination of Lewis bases with alpha, beta-unsaturated carbonyls enables the in-situ generation of enolates, eliminating the need for strong Bronsted bases. This approach has been widely employed in arylation reactions in various contexts. This conceptual article provides an overview of the developed strategies, highlighting their features.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Levente Homolya, David Antal, Mate Nagy, Eva Juhasz-Toth, Marietta Toth, Attila Benyei, Laszlo Somsak, Laszlo Juhasz
Summary: The reactivity of O-peracetylated and O-perbenzoylated 1-COOMe, 1-CONH2 and 1-CN-substituted glycals against O-, S-, N-, and C-nucleophiles in the presence of Lewis acids was investigated. The results showed that the stereoselectivity of the formed products varied with different nucleophiles.
CARBOHYDRATE RESEARCH
(2022)
Article
Chemistry, Organic
Feixue Xue, Xiangyu Chen, Zhengjie He
Summary: A diethyl phosphite mediated reductive [1 + 4] annulation reaction provides an effective and simple method to prepare polysubstituted 2,3-dihydrofurans bearing a quaternary carbon center.
Article
Chemistry, Organic
Rajendra K. Mallick, Srinivas Vangara, Nagarjuna Kommu, Tirumaleswararao Guntreddi, Akhila K. Sahoo
Summary: This paper describes a novel Cu(II)-catalyzed rearrangement reaction for the synthesis of a series of synthetically important α-(m-substituted phenol)-α,β-unsaturated ketones, with a wide scope of functional group tolerance and synthetic viability. The synthesis of α,β-unsaturated ketones is also demonstrated in this study.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Song Xi, Jiawei Dong, Haohua Chen, Qiuyan Dong, Jiao Yang, Qiuyuan Tan, Changhui Zhang, Yu Lan, Min Zhang
Summary: The study presents a silver-catalyzed domino generation and [2,3]-sigmatropic rearrangement of ammonium ylides, leading to the stereoselective synthesis of chiral azabicycles with high enantiomeric purity (up to 99% ee). Experimental findings suggest that residual water in the reaction system plays a crucial role in facilitating the mild reaction conditions. In addition to silver salts, a stoichiometric amount of nonmetallic I-2 has also been successfully employed for the same reaction.
Article
Chemistry, Multidisciplinary
Naresh Bhuma, Ludivine Lebedel, Hiroki Yamashita, Yutaka Shimizu, Zahra Abada, Ana Arda, Jerome Desire, Bastien Michelet, Agnes Martin-Mingot, Ali Abou-Hassan, Masahiro Takumi, Jerome Marrot, Jesus Jimenez-Barbero, Aiichiro Nagaki, Yves Bleriot, Sebastien Thibaudeau
Summary: Ferrier's research in 1962 on the transformation of glycals into unsaturated glycosyl derivatives involved an alpha,beta unsaturated glycosyl cation. Through NMR-based structural analysis and DFT calculations, this elusive ionic species was characterized, leading to the synthesis of unsaturated nitrogen-containing C-aryl glycosides and C-alkyl glycosides under different conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Ram Naresh Yadav, Aarif Latif Shaikh, Bimal Krishna Banik
Summary: In this study, microwave-induced iodine-catalyzed glycosylation of alcohols with glycals derived from galactose and glucose was conducted, producing a mixture of α- and 0-glycosides in good yields.
HETEROCYCLIC LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Shintaro Ishida, Kengo Sakamoto, Ryo Kobayashi, Takeaki Iwamoto
Summary: This study reports the reactions of silanone with triarylboranes to form boroxysilanes. Experimental results and computational studies show that the electrophilicity of the unsaturated silicon atom is enhanced by the complexation of silanone with triarylboranes, and subsequent aryl migration from the boron atom to the electrophilic silicon atom takes place.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Anselme Geulin, Yann Bourne-Branchu, Kawther Ben Ayed, Thomas Lecourt, Antoine Joosten
Summary: 3-Amino-3-deoxyglycosides are important nitrogen-containing sugars, with many important ones having a 1,2-trans configuration. The synthesis of 3-amino-3-deoxyglycosyl donors that can form a 1,2-trans glycosidic linkage is a significant challenge due to their biological applications. This work presents a new sequence involving Ferrier rearrangement and subsequent aza-Wacker cyclization for the rapid synthesis of orthogonally protected 3-amino-3-deoxyglycals. Additionally, the epoxidation/glycosylation of a 3-amino-3-deoxygalactal derivative was successfully achieved with high yield and diastereoselectivity, demonstrating FAWEG as a new approach for accessing 1,2-trans 3-amino-3-deoxyglycosides.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Peiran Chen, Xueqi Dai
Summary: A series of 3-Se 1,2-unsaturated glucosides were successfully synthesized using Hf(OTf)(4) as the catalyst with alkyl(aryl) hydroselenides as the nucleophile precursors, showing good yield under specific conditions.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Physical
Hajime Maeda, Saki Nakamura, Taniyuki Furuyama, Masahito Segi
Summary: The reaction of 1-naphthyl naphthylmethyl ethers 1 and 2 with Lewis acids in CH2Cl2 resulted in rearrangement of the naphthylmethyl group to different positions of the naphthalene ring. The rearrangement of 2-naphthyl ethers 3 and 4 proceeded to the 1-position. Irradiation of compound 1 in benzene solution led to rearrangement at the 4-position, while rearrangement of compound 2 occurred at the 2- and 4-positions. The regioselectivity of the reactions can be explained by charge density, spin density, steric hindrance, and solvent cage effect.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Physical
Yao Luo, Qi Wei, Liangkun Yang, Yuqiao Zhou, Weidi Cao, Zhishan Su, Xiaohua Liu, Xiaoming Feng
Summary: The synthesis of chiral ketones has been a significant focus in chemistry research. In this study, researchers successfully achieved a highly selective radical hydroacylation reaction for α-substituted α,β-unsaturated carbonyl compounds using anthraquinone photocatalyst and chiral N,N'-dioxide/metal complexes. This method provides a mild and robust approach to access a wide range of chiral ketones with α-tertiary stereocenters.
Article
Biochemistry & Molecular Biology
Rohit Sai Reddy Konada, Lakshmi Surekha Krishnapati, Venugopal Ashapogu, Chung-Hung Lin, Siva Kumar Nadimpalli
COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY B-BIOCHEMISTRY & MOLECULAR BIOLOGY
(2020)
Article
Chemistry, Medicinal
Punsaldulam Dashnyam, Hsien-Ya Lin, Chia-Yu Chen, Shijay Gao, Lun-Fu Yeh, Wei-Che Hsieh, Zhijay Tu, Chun-Hung Lin
JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Yu-Rong Chen, Annavareddi Naresh, Suh-Yuen Liang, Chun-Hung Lin, Rong-Jie Chein, Hsiao-Ching Lin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Medicinal
Zheng-Sheng Lai, Teng-Kuang Yeh, Yu-Chi Chou, Tsu Hsu, Cheng-Tai Lu, Fang-Chun Kung, Ming-Yen Hsieh, Chun-Hung Lin, Chiung-Tong Chen, Che-Kun James Shen, Weir-Torn Jiaang
Summary: A more potent inducer, compound 13a, was discovered in this study, which can efficiently induce gamma-globin gene expression at non-cytotoxic concentrations and ameliorate anemia and related symptoms in SCD mice through oral administration.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Hajjaj H. M. Abdu-Allah, Shang-Chuen Wu, Chun-Hung Lin, Yu-Yao Tseng
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Organic
Nitish Verma, Zhijay Tu, Ming-Shiuan Lu, Shih-Hao Liu, Septila Renata, Riping Phang, Peng-Kai Liu, Bhaswati Ghosh, Chun-Hung Lin
Summary: Efficient synthesis of type I LacNAc oligosaccharides was achieved through chemoselective glycosylation, optimizing conditions based on relative reactivity values (RRVs) measurements. The study showed that elongation of glycan chains should proceed from the reducing to the nonreducing end for better yields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biology
Hsien-Ya Lin, Chia-Yu Chen, Ting-Chien Lin, Lun-Fu Yeh, Wei-Che Hsieh, Shijay Gao, Pierre-Alain Burnouf, Bing-Mae Chen, Tung-Ju Hsieh, Punsaldulam Dashnyam, Yen-Hsi Kuo, Zhijay Tu, Steve R. Roffler, Chun-Hung Lin
Summary: This study reports the development of uronic isofagomine derivatives as potent inhibitors of bacterial beta-glucuronidases, especially E. coli and C. perfringens. The best inhibitor, C6-nonyl UIFG, shows high selectivity for E. coli GUS over human GUS and effectively reduces irinotecan-induced diarrhea in mice without damaging intestinal epithelial cells. The study may enhance the development of inhibitors for microbial GUS in colorectal cancer therapy to minimize the side effects of irinotecan treatment.
COMMUNICATIONS BIOLOGY
(2021)
Article
Multidisciplinary Sciences
Tzu-Han Lo, Hung-Lin Chen, Cheng- Yao, I-Chun Weng, Chi-Shan Li, Chi-Chun Huang, Nien-Jung Chen, Chun-Hung Lin, Fu-Tong Liu
Summary: The study demonstrates that galectin-3 enhances caspase-4/11 activation and oligomerization through binding with LPS, resulting in intensified pyroptosis. This finding provides potential opportunities for new therapeutic interventions in host resistance against bacterial infections.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2021)
Article
Chemistry, Organic
Chia-Chen Chang, Hau-Ming Jan, Chieh-Jen Tseng, Soumik Mondal, Andualem Bahiru Abera, Ming-Yen Hsieh, Tsai-Chen Yang, Sasikala Muthusamy, Sheng-Cih Huang, Chun-Hung Lin, Kwok-Kong Tony Mong
Summary: This study reports the isolation and stereochemical determination of the predominant native cholesteryl 6-O-phosphatidyl alpha- glucoside (CPG) from Helicobacter pylori. The authors used a combination of metabolic isolation and enzymatic degradation to obtain the native lactobacillic acid for stereochemical determination. The absolute stereochemistry of the acid was found to be 11R and 12S. Using this information, the authors achieved the total synthesis of predominant native CPG and other derivatives.
Article
Chemistry, Multidisciplinary
Soumik Mondal, Chieh-Jen Tseng, Janet Jia-Yin Tan, Ding-Yuan Lin, Hsien-Ya Lin, Jui-Hsia Weng, Chun-Hung Lin, Kwok-Kong Tony Mong
Summary: We developed a versatile strategy to synthesize different classes of sulfoglycolipids and investigated their immunomodulatory properties on host innate immunity response.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Po-Yen Chen, Yi-Ting Chiang, Min-Tsang Hsieh, You-Cheng Hseu, Chun-Hung Lin, Hui-Chang Lin
Summary: Spiro[pyran-4-quinolines] were synthesized from exo-glycals in two steps with overall yields of 60-72%. The obtained compounds showed high stereoselectivity and could be synthesized in one-pot using exo-galactals as starting materials at 75 degrees C.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Cell Biology
Sasikala Muthusamy, Hau-Ming Jan, Ming-Yen Hsieh, Soumik Mondal, Wen-Chun Liu, Yi-An Ko, Wei-Yuan Yang, Kwok-Kong Tony Mong, Guang-Chao Chen, Chun-Hung Lin
Summary: The study revealed that CAG enhances the internalization of H. pylori in host cells, disrupts autophagy flux, and reduces lysosomal biogenesis.
JOURNAL OF BIOMEDICAL SCIENCE
(2021)
Article
Biochemistry & Molecular Biology
Ming-Hsiang Hong, Wei-Han Lin, I-Chun Weng, Yu-Hsien Hung, Hung-Lin Chen, Huan-Yuan Chen, Peilin Chen, Chun-Hung Lin, Wei Yuan Yang, Fu-Tong Liu
Article
Biology
Hau-Ming Jan, Yi-Chi Chen, Tsai-Chen Yang, Lih-Lih Ong, Chia-Chen Chang, Sasikala Muthusamy, Andualem Bahiru Abera, Ming-Shiang Wu, Jacquelyn Gervay-Hague, Kwok-Kong Tony Mong, Chun-Hung Lin
COMMUNICATIONS BIOLOGY
(2020)
Article
Biochemistry & Molecular Biology
Fang-Yen Li, I-Chun Weng, Chun-Hung Lin, Mou-Chieh Kao, Ming-Shiang Wu, Huan-Yuan Chen, Fu-Tong Liu
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.
