Article
Chemistry, Organic
Jiamin Wang, Sujuan Shuai, Lishe Gan, Yongxin Luo, Huimin Jin, Lingfeng Chen, Dong Zou, Guang Liang, Patrick J. Walsh, Jie Li
Summary: This study presents a highly chemoselective amidation method for the Boc and amide groups of N-R-N-Boc arylamides. The method is practical and easy to carry out, allowing for the preparation of N-aroylureas or imides in high yields without the use of transition metals. The choice of base determines the reactivity of the different carbonyl groups, with arylamides undergoing amidation with (KOBu)-Bu-t and imides being produced with LiOH. DFT studies are employed to investigate the mechanisms involved. These chemoselective methods are expected to be valuable in synthetic and medicinal chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Biochemistry & Molecular Biology
Dong Geun Jo, Changeun Kim, Sinjae Lee, Sooyeon Yun, Seewon Joung
Summary: This study presents a methodology for the synthesis of cyclic N-acyl amidines from easily accessible N-heteroarenes. The reaction utilizes N-silyl enamine intermediates, obtained through hydrosilylation, for the [3 + 2] cycloaddition step. By evaluating different acyl azides, a reasonable yield of cyclic N-acyl amidines was achieved. The reactivity of each step and the electronic nature of the substrates were analyzed using in situ nuclear magnetic resonance spectroscopy, providing insight into the reaction mechanism.
Article
Chemistry, Organic
Yuan Zhong, Xiaoqiang Zhao, Xiaoyun Zhao, Dan Zhang, Wenli Li, Shouhui Wei, Fanhong Liu, Jihua Yu, Guichen Li, Dandan Wang
Summary: The green and atom-economical synthesis of functionalized 2-pyrrolines with two contiguous stereocenters was achieved using a catalytic amount of bifunctional chiral squaramide in a one-pot annulation reaction, providing good yields under mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Shrikant D. Tambe, Cheol Hyeon Ka, Ho Seong Hwang, Jaehan Bae, Naeem Iqbal, Eun Jin Cho
Summary: The synthesis of highly functionalized chiral 3-pyrrolines is important for the production of natural and synthetic bioactive molecules. Previous methods using allenoates could not synthesize 3,4-disubstituted 3-pyrrolines. This study presents a novel approach to produce 2,3,4-trisubstituted chiral 3-pyrrolines through a highly stereoselective process using a Ni-II/Fc-i-PrPHOX catalytic system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yundong Wu, Lei Guo, Yuxuan Liu, Jiannan Xiang, Jun Jiang
Summary: A selective and mild method for the synthesis of N-aryl amides was developed in this study, with good yields obtained in water from commercially available nitroarenes and acyl halides. The reaction, with Fe dust as the only reductant and additive, can be easily performed on a large scale.
Article
Chemistry, Organic
Gopal Rana, Abhishek Kar, Sandip Kundal, Dulal Musib, Umasish Jana
Summary: In this study, a new method for the synthesis of substituted 3-acylindoles using DDQ as a catalyst is reported. The method involves the regioselective oxo-functionalization of C-3 alkyl-/aryllidine indolines using catalytic DDQ in combination with Fe(NO3)3 center dot 9H2O and molecular oxygen as co-catalysts. The method is general and offers high yields with varieties of functional groups tolerance. Furthermore, molecular docking studies demonstrate the potential of the synthesized ligands to inhibit the RdRp complex of SARS-CoV-2.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Gareth E. Boer, Shane M. Hickey, Alysha G. Elliott, Frederick M. Pfeffer
Summary: Convergent, late-stage introduction of acylguanidine moieties is a useful strategy for rapid development of novel compounds. In this study, a method for synthesizing a range of acylguanidine compounds was reported, and it was successfully applied to generate a new antimicrobial agent.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Jin Zhang, Pei Zhang, Yangmin Ma, Michal Szostak
Summary: This study reports a novel solvent-free method for synthesizing ketones with high selectivity from acyl chlorides and boronic acids. The reaction takes place in the solid state, without the use of solvents, and has a short reaction time, demonstrating excellent selectivity for C(acyl)-Cl bond cleavage.
Article
Chemistry, Organic
Xue-Bing Chen, Shun-Tao Huang, Jie Li, Qi Yang, Li Yang, Fuchao Yu
Summary: This novel synthetic strategy uses base-catalyzed annulation to selectively generate highly functionalized aposafranones and their N-oxides, offering a new method in organic synthesis and biology.
Article
Biochemistry & Molecular Biology
Xue-Min Jia, Cheng Cheng, Ting Liu, Yong-Long Zhao, Bing Guo, Lei Tang, Yuan-Yong Yang
Summary: This study synthesized 39 N-acyl-2-aminopyrimidine derivatives and tested their inhibition efficacy on A. baumannii biofilm. Some of the analogues showed potential clinical significance and were demonstrated to be quorum sensing inhibitors.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Jie Li, Jiaqi Yao, Lingfeng Chen, Dong Zou, Patrick J. Walsh, Guang Liang
Summary: The imide moiety is a well-known structural motif in bioactive compounds and can be utilized as a building block in various processes. A unique feature of the presented method is the use of two different electrophilic acylating reagents, resulting in the formation of unsymmetrical imides with excellent chemoselectivity. Additionally, symmetric imides can be accessed when N-acylglutarimides are used as acylation reagents under similar reaction conditions.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Philippe N. Bolduc, Magnus Pfaffenbach, Vanna D. Blasczak, Steven R. Mathieu, Emily A. Peterson
Summary: This article presents an efficient synthesis method for a variety of N-substituted 2-pyridones, using ethyl nitroacetate and readily available primary amine building blocks, which can be widely used in large-scale and parallel medicinal chemistry.
Article
Chemistry, Applied
Biao Zhang, Pan Zhou, Hui Xu, Jiuzhong Huang, Yulin Sun, Donghan Liu, Fuchao Yu
Summary: A copper(II)-mediated intermolecular radical [3+2] annulation of N,N-dimethyl enaminones has been developed, providing access to 5-acyl-3-furancarboxaldehydes with good yields and broad substrate scope. This reaction allows the formation of multiple new bonds through a radical cyclization process, showing potential application value in industry as demonstrated by gram-scale synthesis and application research.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Applied
Motohiro Yasui, Naoko Tahara, Hiroshi Matsubara, Norihiko Takeda, Masafumi Ueda
Summary: This study developed a sequential gold-catalyzed reaction for synthesizing 4-aryl-3-(2H)-isoxazolones with a hydroxy group. The method allows the introduction of an aryl and hydroxy group in a single procedure, exhibiting good chemoselectivity and tolerance towards reactive functional groups.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Xiaokun Zhang, Xiuqing Song, Jiwen Shi, Hong Yan, Nana Tian
Summary: The photocycloaddition of 1,4-dihydropyridines (1,4-DHPs) is a main approach for synthesizing structurally complex compounds, which serve as important intermediates for the preparation of cage compounds. This study aimed to investigate the effect of the structural characteristics on the chemoselectivity in [2 + 2]/[3 + 2] photocycloaddition of 1,4-DHPs. The research found that steric hindrance and chirality at specific positions in 1,4-DHPs play crucial roles in determining the chemoselectivity of the reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Wesley J. Olivier, Jason A. Smith, Alex C. Bissember
Summary: This article showcases the utility of pyrrole-based approaches in facilitating the total synthesis of pyrrolidine- and pyrrolidinone-containing alkaloids and related molecules, using examples from the Aspidosperma, Stemona, and batzelladine families.
Article
Chemistry, Medicinal
Thinley Gyeltshen, Gregory J. Jordan, Jason A. Smith, Alex C. Bissember
Summary: The first natural product isolation studies of Nothofagus gunnii and Nothofagus cunninghamii revealed that N. gunnii is a rich source of flavonoid, chalcone and stilbene compounds, while primarily hydroxyflavonoid compounds are found in N. cunninghamii. The isolated phytochemicals are consistent with the evolutionary relationships among Nothofagus species.
Article
Chemistry, Organic
Wesley J. Olivier, Jason A. Smith, Alex C. Bissember
Summary: This article presents the research on Parvistemoamide, including its discovery and synthetic studies. The results show that the structure of Parvistemoamide is similar to the Stemona alkaloid Stemoamide.
Article
Plant Sciences
Thinley Gyeltshen, Bianca J. Deans, Curtis C. Ho, Nathan L. Kilah, Jason A. Smith, Alex C. Bissember
Summary: This study isolated two previously unreported furanosesquiterpenes and three unprecedented gamma-lactone-containing analogues from three Myoporum species. Additionally, nine previously reported furanosesquiterpenes and five other natural products were also isolated. Three distinct types of furanosesquiterpene structures were observed in each of these Myoporum species. Four sesquiterpene natural products, including the lactam-containing sesquiterpene myoporumine A, were synthesized from (-)-ngaione in two steps for each case.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Chemistry, Organic
Liam M. Joyce, Stephen A. Moggach, Christopher J. T. Hyland, Stephen G. Pyne, Scott G. Stewart
Summary: A nickel-catalyzed tetradehydro-Diels-Alder reaction of (E)-3-ene-1,8-diynes has been developed for the synthesis of isoindolines, dihydroisobenzofurans, and tetrahydroisoquinolines. Air-stable nickel catalysts, including novel nickel(0)-phosphite catalysts, were employed in this study. Additionally, the mechanism of trapping nickellacycle intermediates with pinacolborane to yield vinyl boronates was discussed to gain insights into the initial cycloisomerization process.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Lillian A. de Ceuninck van Capelle, Steven M. M. Wales, James M. M. Macdonald, Megan Kruger, Christopher Richardson, Michael G. G. Gardiner, Christopher J. T. Hyland
Summary: In this study, bench-stable benzoazepine-fused isoindoles were synthesized via oxidation from isoindoline precursors. The stereochemistry and conformational folding were examined using isoindoles 5d-f as models. The factors contributing to the stability of atropisomers were elucidated using various techniques including chiral UHPLC, X-ray crystallography, H-1 NMR spectroscopy, and DFT calculations, revealing the role of steric hindrance and folded conformation in stabilizing the system.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Adriana R. Dutra-Nobre, Wesley J. Olivier, Bianca J. Deans, Nathan L. Kilah, Fernando Maya Alejandro, Jason A. Smith, Alex C. Bissember
Summary: Natural product isolation studies on Dodonaea viscosa revealed significant intraspecific variation in terpene profiles across this species. A total of 14 ent-labdane diterpenoids (including seven previously unreported compounds), four ent-kauranes (including one previously unreported compound), one rare norhopene, and two previously unreported monoterpenoid wax esters were isolated. The proposed structures were elucidated using various spectroscopic techniques and supported by additional analyses such as mass spectrometry and X-ray crystallography.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Samuel D. Zarfos, Bianca J. Deans, Curtis C. Ho, Gregory J. Jordan, Jason A. Smith, Alex C. Bissember
Summary: This study focused on the isolation of natural products from eight Tasmanian Proteaceae species and three Australian Proteaceae species. Two previously unreported natural products and four rare arbutin esters were identified, supporting the idea that these unique arbutin esters can serve as markers for the chemical evolution of plant species within the Proteaceae family.
CHEMISTRY & BIODIVERSITY
(2023)
Article
Chemistry, Multidisciplinary
Philip J. Chevis, Chi Bong Eric Chao, Christopher Richardson, Christopher Hyland, Richmond Lee, Stephen G. Pyne
Summary: The crotylation reactions of chiral α-F, α-OBz and α-OH aldehydes were carried out under Petasis-borono-Mannich conditions using (E)- or (Z)-crotylboronates and primary amines. The reactions resulted in γ-addition products with high diastereoselectivity and enantioselectivity. The stereochemical outcomes of the reactions could be explained using transition state models and were supported by DFT calculations. Representative products were transformed into highly functionalized 1,2,3,6-tetrahydropyridines and 3H-oxazolo[3,4-a]pyridine-3-ones, which are valuable scaffolds in synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Andrew J. Tague, Quoc Hoang Pham, Christopher Richardson, Stephen G. Pyne, Christopher J. T. Hyland
Summary: A formal palladium-catalyzed decarboxylative (4+2) cycloaddition reaction has been developed to produce highly valuable tetrahydroquinolines in moderate to excellent yields with high diastereoselectivity. The reaction protocol can tolerate a range of substituted 2-nitro-1,3-enynes, which are an under-utilized class of dipolarophiles. The tetrahydroquinoline products obtained feature numerous pendant functionalities for further synthetic manipulations.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Chi Bong Eric Chao, Stephen G. Pyne, Christopher J. T. Hyland, Richmond Lee
Summary: Density functional theory has been used to elucidate the mechanistic details of arylative cyclization reactions with arylboronic acids. The modeling results are in agreement with experimental observations and explain the high diastereo- and enantioselectivity at high reaction temperature. Additionally, a novel mechanism for base-free organoboron transmetalation has been revealed.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Applied
Wilhelm R. Glomm, Peter P. Molesworth, Betul Yesiltas, Charlotte Jacobsen, Heidi Johnsen
Summary: The molecular characteristics of food-grade polysaccharide gum acacia can vary depending on the source, which impacts its behavior as a thickener, emulsifier, and wall material in microencapsulation. In this study, five acacia gums from different sources were compared in terms of molecular weight distribution, interfacial tension, microencapsulation of salmon oil, and oxidative stability of the oil. Three of the tested acacia gums resulted in stable microcapsules with high encapsulation yield and improved oxidative stability compared to the remaining two gums.
FOOD HYDROCOLLOIDS
(2023)
Article
Chemistry, Multidisciplinary
Quoc Hoang Pham, Andrew J. Tague, Christopher Richardson, Michael G. Gardiner, Stephen G. Pyne, Christopher J. T. Hyland
Summary: A Pd-catalysed (3 + 2) cycloaddition reaction of bis(trifluoroethyl) 2-vinyl-cyclopropane-1,1-dicarboxylate (VCP) with cyclic sulfamidate imine-derived 1-azadienes (SDAs) has been developed, leading to highly functionalized spiroheterocycles with three contiguous stereocentres, including a tetrasubstituted carbon bearing an oxygen functionality. The geminal trifluoroethyl ester groups can be selectively manipulated to afford spirocycles with four contiguous stereocentres. Additionally, reduction of the imine moiety can introduce a fourth stereocentre and expose a 1,2-amino alcohol functionality.
Review
Polymer Science
Melissa K. Stanfield, Rhiannon S. Terry, Jason A. Smith, Stuart C. Thickett
Summary: This review focuses on the use of levoglucosan (LGA) and levoglucosenone (LGO) obtained from cellulose pyrolysis in materials synthesis. It presents various types of polymers, including polyesters, polysaccharides, metathesis-based polymers, and photopolymerized thermosets. The sustainability and environmental impact of these syntheses are also discussed.
Review
Biochemistry & Molecular Biology
Wesley J. Olivier, Jackson S. Henneveld, Jason A. Smith, Bill C. Hawkins, Alex C. Bissember
Summary: This review presents the key strategies and overall progress made in the synthesis of Stemona alkaloids and related compounds since 2009. Case studies are grouped by alkaloid class, showcasing the advancements in this field. Structural reassignments reported during this period are also identified.
NATURAL PRODUCT REPORTS
(2022)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
