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, Multidisciplinary
Jia-Xuan Liu, Shi-Peng Zhang, Feng-Sen Sun, Hui Li, Ya-Ling Gong, Shi-Chao Lu, Shu Xu
Summary: In this study, Naphthospironone A, a polyhydroxy cagelike bioactive natural product, was synthesized for the first time. The spiro[bicyclo[3.2.1]octane-pyran] core was constructed by an acid-promoted epoxide-opening lactonisation and a base-induced intramolecular aldol-type cyclisation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jeremy Nugent, Alistair J. Sterling, Nils Frank, James J. Mousseau, Edward A. Anderson
Summary: Bicyclo[1.1.1]pentanes (BCPs) are synthesized efficiently using organophotoredox and hydrogen atom transfer catalysis, allowing for the preparation of alpha-quaternary BCPs. The products can be further transformed into a variety of useful derivatives, including enantioenriched BCPs.
Article
Chemistry, Multidisciplinary
Weiping Zhou, Arnaud Voituriez
Summary: A cationic gold(I)-catalyzed asymmetric [3,3]-sigmatropic rearrangement of sulfonium leads to the formation of cyclopentenones with a C4-quaternary stereocenter after cyclization. This methodology was successfully applied to the efficient total synthesis of five natural sesquiterpenoids, demonstrating moderate to good yields and excellent enantiomeric excesses in 26 examples.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Lihong Xu, Anan Wang, Xu Shi, Qian He, Tao-Shan Jiang
Summary: This study describes the HOAc-promoted construction of chroman-4-ones with a sulfur atom and an a-carbonyl quaternary carbon center directly from ortho-hydroxyacetophenones and DMSO. In these reactions, DMSO is activated by HOAc and provides three different units in the target molecules. The reaction displays good substrate scope and reaction yields with a series of substitutes.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Lilla Koser, Vivian Miles Lechner, Thorsten Bach
Summary: The first chemical total synthesis of the highly oxygenated polyketide enterocin has been achieved using a late-stage biomimetic reaction cascade. The synthesis involved assembling a pivotal precursor from three readily available building blocks, with a chiral dithioacetal representing the core fragment. Additional building blocks were attached to both ends of the core fragment through aldol reactions, leading to the installation of four stereogenic centers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Moinul Haque Sahana, Debobrata Paul, Himangshu Sharma, Rajib Kumar Goswami
Summary: A convergent route for the asymmetric total synthesis of antibacterial macrolide sorangiolide A has been developed, incorporating key reactions to address the low intensity of C1 and C2 center NMR signals and revealing the possible forms of existence for the natural product in solution.
Article
Chemistry, Organic
Chang-Lun Lo, Pavan Sudheer Akula, Bor-Cherng Hong, Gene-Hsiang Lee, Su-Ying Chien
Summary: The first total synthesis of ulodione A has been achieved through a series of reactions, including the key-step reactions of DIPEA-promoted dialkytion of 1,3-cyclopentadione with a bromonitroolefin and DABCO promoted/catalytic semipinacol-like ring-expansion rearrangement, with regioselective transformation of the nitrocyclohexane intermediates to their cyclopentenone counterparts. The structures of six products were confirmed by X-ray crystallography.
Article
Chemistry, Physical
Jialin Qi, Tingting Song, Zhenning Yang, Shuzhe Sun, Chen-Ho Tung, Zhenghu Xu
Summary: A stereodivergent synthesis of chiral beta-lactams with contiguous tertiary/quaternary/tertiary stereocenters has been achieved. The strategy involves a Cu/Ir-catalyzed three-component interrupted Kinugasa allylic alkylation reaction, which provides access to four of the eight possible stereoisomers with high yields and >99% ee. The key features are the asymmetric simultaneous dual metal-catalyzed cascade reactions with stereoselective coupling of highly transient organometallic intermediates.
Article
Chemistry, Multidisciplinary
Debasish Ghorai, Aleria Garcia-Roca, Balazs L. Toth, Jordi Benet-Buchholz, Arjan W. Kleij
Summary: This article reports the regio- and enantioselective synthesis of chiral 1,5-dienes featuring quaternary stereocenters via nickel-promoted reductive homoallylic coupling. The developed methodology can selectively form unusual branched regioisomers and improve the enantiomeric and chemo-selectivity of the products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Junyang Liu, Ying Chen, Hendrik Luesch, Tao Ye
Summary: The first asymmetric total synthesis and validation of the structural assignment of des-thiomethyllooekeyolide A (3) is described, which involves a Shiina macrolactonization and a late-stage pyran-hemiketal formation. The eight stereogenic centers of the C16-polyketide chain were installed by sequential aldol and crotylation reactions.
Article
Chemistry, Multidisciplinary
Hai-Hua Lu, Kang-Ji Gan, Fu-Qiang Ni, Zhihan Zhang, Yao Zhu
Summary: The concise total synthesis of salimabromide was achieved using a series of novel reactions, which allowed for the construction of its unique carbon skeleton and stereocenters.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Masahito Yoshida, Yuhi Okoshi, Hideo Kigoshi
Summary: A concise total synthesis of metacridamides A and B was achieved through repetitive vinylogous Mukaiyama aldol reactions and ynamide-mediated macrolactonization. The spectral data of the synthetic products matched those of the natural compounds, leading to the reassessment of the absolute configuration of the C-9 position as S.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Xin Qin, Jinhai Zhang, Zhan-Yong Wang, Yimei Song, Yixiao Yang, Wenhai Zhang, Hongxin Liu
Summary: In this study, a aldol/Michael cascade reaction on the beta,gamma-positions of alpha,beta-unsaturated ketones with ketoamides to construct bicyclic lactams via DBU catalysis has been developed. The substrates exhibited high regio- and diastereoselectivities and yielded moderate to good results (32 examples). Control experiments showed that the hydrogen of the amide played a key role.
Article
Chemistry, Organic
Joshua A. Malone, Satish Chandra Philkhana, Jacob R. Stepherson, Fatimat O. Badmus, Frank R. Fronczek, Rendy Kartika
Summary: This article describes a new synthetic reaction that can generate all-carbon bisquaternary centers at the opposing side of alpha-carbons in cyclohexanone with four different substituents in a controlled manner.
Review
Chemistry, Inorganic & Nuclear
Hongil Jo, Xinglong Chen, Hee-Seung Lee, Kang Min Ok
Summary: Chirality is a key topic in chemistry due to its unique stereochemical properties and asymmetric structure. Chiral materials may exhibit second-harmonic generation properties, and efficient SHG can be achieved by controlling the arrangement of noncentrosymmetric chromophores.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2021)
Article
Nanoscience & Nanotechnology
Yonghyeon Kim, Young Wook Lee, Seunghoon Lee, Jintaek Gong, Hee-Seung Lee, Sang Woo Han
Summary: This study reported a new strategy for the synthesis of Pd-Pt-Ag ternary alloy HNSs through a self-templating approach. By simultaneously reducing multiple metal precursors in the presence of CTAC, the morphology of HNSs can be controlled, with the size and hollowness of HNSs adjustable.
ACS APPLIED MATERIALS & INTERFACES
(2021)
Article
Chemistry, Multidisciplinary
Seoneun Jeong, Lianjin Zhang, Jaewook Kim, Jintaek Gong, Jonghoon Choi, Kang Min Ok, Yunho Lee, Sunbum Kwon, Hee-Seung Lee
Summary: This study presents the first metal-coordination-mediated assembly of beta-peptide foldamers with 12-helical folding propensity, resulting in unique entangled metal-peptide frameworks. The formation of network structures is accompanied by notable conformational distortions of the foldamer ligands. This work is expected to be an important benchmark for further structural evolution and mechanistic investigation in the field of metal-peptide frameworks.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Taehyung Kim, Se Hun Joo, Jintaek Gong, Sungho Choi, Ju Hong Min, Yongchul Kim, Geunsik Lee, Eunji Lee, Soojin Park, Sang Kyu Kwak, Hee-Seung Lee, Byeong-Su Kim
Summary: In this study, highly crystalline PICs with various pore dimensions were successfully synthesized under geomimetic hydrothermal conditions. The solubility of the oligomeric intermediates under hydrothermal conditions was found to affect the stacking structures of the crystalline PICs. Additionally, the synthesized PICs show promising potential as an anode material in lithium-ion batteries due to their unique redox-active properties and high surface area.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Rokam Jeong, Jae-Hoon Eom, Jintaek Gong, Minsang Kang, Jaewook Kim, Hee-Seung Lee
Summary: This study reports the first example of programmed radial assembly of anisotropic microparticles derived from a helical foldamer with a C-terminal cysteine residue. Surface-exposed thiols play a crucial role in facilitating interparticle hydrogen bonding to form higher-order structures in an aqueous solution.
Review
Chemistry, Multidisciplinary
Byeonghoon Choi, Dongwoo Shin, Hee-Seung Lee, Hyunjoon Song
Summary: Metal oxide semiconductors are suitable for chemiresistive gas sensors, with p-type oxide semiconductors being improved through nanostructuring and forming p-n heterojunctions for enhanced sensitivity at low temperatures. These materials are gaining attention as advanced gas sensing materials for environmental and healthcare monitoring, especially when combined with strategies like light activation and sensor arrays for exclusive gas detection at ultra-low concentrations.
Article
Chemistry, Multidisciplinary
Chang-Hee Whang, Jungwoo Hong, Dohyeon Kim, Hong Ryu, Wonsik Jung, Youngju Son, Hyeongseop Keum, Jinjoo Kim, Hocheol Shin, Eugene Moon, Ilkoo Noh, Hee-Seung Lee, Sangyong Jon
Summary: This study reports a library of glycocalyx-mimicking nanoparticles for screening and identification of cancer-targeting nanomedicines. The researchers found that certain nanoparticles selectively targeted different tumors and exhibited potent therapeutic effects. The results suggest that this nanoparticle library has a versatile application potential beyond cancer treatment.
ADVANCED MATERIALS
(2022)
Article
Chemistry, Organic
Thomas T. Kim, Chungwoo Lee, Dongwook Kim, Hee-Seung Lee, Sunkyu Han
Summary: In this paper, we present the synthesis and reactivity of 1-hydroxyherquline A, and discuss the challenges encountered during its conversion to herquline A. These findings provide valuable insights for future research and synthesis of herquline A.
Review
Biochemistry & Molecular Biology
Seoneun Jeong, Kwonjung Lee, Sung Hyun Yoo, Hee-Seung Lee, Sunbum Kwon
Summary: Metal-peptide networks are structures assembled from short peptides and metal ions, known for their unique and complicated features. However, limitations such as designability, stability, and modifiability have hindered their practical applications. This review summarizes important milestones in the development of crystalline metal-peptide networks and analyzes their structural features and potential applications, providing insights for the development of new metal-peptide networks with more sophisticated structures and novel functions.
Article
Chemistry, Multidisciplinary
Sung Hyun Yoo, Jintaek Gong, Lianjin Zhang, Seoneun Jeong, Jin Kim, Hee-Seung Lee
Summary: This study reported transition metal complexes from an unnatural beta-amino acid, showing different coordination modes and structural features.
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Dohyun Yoo, Chang-Hee Whang, Jungwoo Hong, Dohyeon Kim, Monica Celine Prayogo, Youngju Son, Wonsik Jung, Seojung Lee, Hee-Seung Lee, Sangyong Jon
Summary: Current medications for inflammatory bowel disease (IBD) have limited effectiveness and severe side effects. Therefore, there is an urgent need for novel therapeutic approaches that can specifically target inflamed areas in the gastrointestinal tract with minimal systemic effects. In this study, researchers constructed a library of anti-inflammatory nanoparticles called GlyNPs and evaluated their therapeutic potential in a mouse model of IBD. By attaching bilirubin (BR) to a library of glycopolymers, the researchers identified a candidate GlyNP capable of targeting macrophages in the inflamed colon and effectively alleviating colitis symptoms. These findings suggest that the BR-attached GlyNP library can serve as a platform for identifying anti-inflammatory nanomedicines for various inflammatory diseases.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Danim Lim, Wonchul Lee, Jungwoo Hong, Jintaek Gong, Jonghoon Choi, Jaewook Kim, Seolhee Lim, Sung Hyun Yoo, Yunho Lee, Hee-Seung Lee
Summary: We introduce a novel cyclic β-amino acid, trans-(3S,4R)-4-aminotetrahydrothiophene-3-carboxylic acid (ATTC), as a versatile building block for designing peptide foldamers with controlled secondary structures. Our findings reveal that ATTC-containing foldamers can adopt 12-helical conformations similar to their isosteres and offer the possibility of fine-tuning their properties via post-synthetic modifications. In particular, chemoselective conjugation strategies demonstrate that ATTC provides unique post-synthetic modification opportunities, which expand their potential applications across diverse research areas.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jaewook Kim, Jungwoo Hong, Mi Jeong Park, Hee-Seung Lee
Summary: This groundbreaking research uncovers an approach for crafting chiral channels in metal-peptide networks (MPNs). The strategic integration of foldamer ligands and CuI clusters allows precise, atomic-level modifications. The technique expedites enantiomer discrimination in mixtures and prompts adaptable molecules to adopt specific chiral forms. It promises the potential for multifunctional materials useful in catalysis, drug delivery, and sensing technologies.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Jungwoo Hong, Wonchul Lee, Hee-Seung Lee
Summary: This article presents an optimized method for the stereoselective synthesis of five-membered alicyclic and heterocyclic trans-beta-amino acid derivatives, which allows for high yields and scalable production of the desired building blocks.
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Physical
Jihye Park, Hee-Seung Lee, Hyungjun Kim, Jeong-Mo Choi
Summary: In this study, we assessed the performance of three popular force fields in predicting the conformational propensities of a beta-peptide foldamer. Our results showed the unanimous role of hydrogen bonds in shaping energy landscapes. These findings contribute to the improvement of force fields and understanding the role of solvents in peptide folding, crystallization, and engineering.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
