Article
Chemistry, Multidisciplinary
Jie Xu, Samantha Grosslight, Kyle A. Mack, Sierra C. Nguyen, Kyle Clagg, Ngiap-Kie Lim, Jacob C. Timmerman, Jeff Shen, Nicholas A. White, Lauren E. Sirois, Chong Han, Haiming Zhang, Matthew S. Sigman, Francis Gosselin
Summary: An efficient asymmetric synthesis of a potent KRAS G12C covalent inhibitor, GDC-6036, was reported. The synthesis involved a highly selective Negishi coupling and a series of reaction sequences, leading to the desired compound with a 40% overall yield from the starting materials.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Multidisciplinary Sciences
Lara E. Zetzsche, Jessica A. Yazarians, Suman Chakrabarty, Meagan E. Hinze, Lauren A. M. Murray, April L. Lukowski, Leo A. Joyce, Alison R. H. Narayan
Summary: This study demonstrates the use of cytochrome P450 enzymes for biocatalytic cross-coupling reactions, enabling the formation of sterically hindered biaryl bonds through oxidative C-C bond formation. By engineering the substrate and atroposelectivity of the P450 enzyme, a highly efficient and selective process has been developed.
Article
Dentistry, Oral Surgery & Medicine
A. Rakian, R. Rakian, A. E. Shay, C. N. Serhan, T. E. Van Dyke
Summary: Periodontal disease is a significant global public health problem, and current treatments have limited effectiveness in controlling chronic inflammation. Recent advancements in stem cell research have shown potential in periodontal regeneration, but controlling inflammation remains a challenge. A new study has found that periodontal ligament stem cells release specialized lipid mediators that modulate the immune response and promote resolution of inflammation, tissue repair, and regeneration. Furthermore, the lack of a suitable large animal model has been a limitation in stem cell biology research in periodontology.
JOURNAL OF DENTAL RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Yan-Long Zheng, Pei-Pei Xie, Omid Daneshfar, Kendall N. Houk, Xin Hong, Stephen G. Newman
Summary: A new method has been developed to convert alkyl esters into alkyl ketones, resulting in the synthesis of 65 different alkyl ketones with various functional groups and heterocyclic structures. The study found that catalyst-controlled chemoselectivity could activate the C(acyl)-O bond in the substrate, while density functional theory calculations supported the mechanism of the nickel catalytic cycle.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Miki B. Kurosawa, Kenta Kato, Kei Muto, Junichiro Yamaguchi
Summary: A deoxygenative transformation method was developed for the synthesis of multiply arylated alkanes from various diarylketones. The method involves a phospha-Brook rearrangement of diarylketones by reacting with diphenylphosphine oxide, followed by palladium-catalyzed cross-couplings or a Friedel-Crafts type alkylation. The method also enables the one-pot conversion from arylcarboxylic acids to diarylmethanes and tetraarylethanes, as well as the synthesis of tetraarylmethane and triphenylethane using sequential coupling reactions.
Review
Chemistry, Multidisciplinary
Anna-Carin C. Carlsson, Staffan Karlsson, Rachel H. Munday, Matthew R. . Tatton
Summary: Atropisomerism is a stereochemical phenomenon exhibited by molecules with a rotationally restricted sigma bond. Atropisomers exist as a dynamic mixture and can be interconverted without breaking and reforming bonds. They are frequent targets in medicinal chemistry projects due to their axial chirality and unique 3D structures. However, selecting a single atropisomer presents problems such as interconversion and separation challenges. Chromatography, enzymatic or chiral catalysts can be used for separation, but each method has limitations. This Account discusses the successes, failures, and challenges of developing methods for resolution and synthesis of atropisomeric drug candidates.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Review
Chemistry, Physical
Brijesh S. Kadu
Summary: Palladium has been widely used in the Suzuki-Miyaura cross coupling reaction for over 30 years, but it comes with drawbacks such as high cost, tedious work-ups, product contamination, and metal leaching. In recent years, other metals like Ni, Cu, Co, Fe, Rh, and Ru have attracted attention for their potential in SMCR, allowing for the synthesis of industrially important compounds with various functional groups. This review discusses recent advancements in catalysis related to SMCR, providing valuable insights for researchers in designing synthetic protocols for pharmacophores and drug molecules.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Physical
Yanhui Wang, Xiaotian Qi, Qiao Ma, Peng Liu, Gavin Chit Tsui
Summary: The diastereoselective synthesis of densely functionalized tetrasubstituted (E)-monofluoroalkenes via Pd(0)-catalyzed base-free Suzuki-Miyaura crosscouplings offers a significant method for producing pharmaceutically relevant compounds. Computational studies support the reaction design, revealing an intriguing mechanism of C-F bond activation leading to complete control of stereoselectivity. This method does not require extraneous base assistance, making it a powerful tool for stereocontrolled synthesis of monofluoroalkenes.
Article
Chemistry, Multidisciplinary
Ko Sato, Hiroshi Tanaka
Summary: In this study, a borate-mediated one-pot sequential Suzuki-Miyaura coupling method was successfully used to synthesize various lignan compounds, achieving the synthesis of naturally occurring lignans through asymmetric cyclic hydroboration and a series of reaction steps.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Yoshitaka Matsushima, Kohei Ishii, Alisa Huffaker, Eric A. Schmelz
Summary: The first concise method for the synthesis of zealexin B1, a maize sesquiterpenoid phytoalexin, was developed via Suzuki-Miyaura coupling. The yields of the coupling reaction were significantly different depending on the combination of boronate and triflate coupling partners.
TETRAHEDRON LETTERS
(2022)
Article
Biochemistry & Molecular Biology
Andre J. van der Vlies, Urara Hasegawa
Summary: This article reports a novel strategy to introduce different functional groups to phenylboronic acid (PBA)-containing nanoparticles (BNP) through the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. A new catalytic system was developed to efficiently catalyze Suzuki-Miyaura reactions in water without the need for an organic solvent. The study shows that BNPs can be functionalized with carboxylic acids, aldehyde, and hydrazide groups while maintaining their original morphology, and the functionalized BNP demonstrates the capability of drug delivery by releasing hydrogen sulfide (H2S) in cell lysate.
Article
Chemistry, Applied
Mostafa Koolivand, Mohsen Nikoorazm, Arash Ghorbani-Choghamarani, Bahman Tahmasbi
Summary: By utilizing citric acid, a chelating agent with three carboxylic groups, Cu-CA-MOF was prepared and characterized. The MOF exhibited acceptable BET surface area and geometric polyhedral shapes in various analyses, and displayed catalytic activity in Suzuki-Miyaura cross-coupling and chemoselective oxidation reactions.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Asma Hrizi, Manon Cailler, Moufida Romdhani-Younes, Yvan Carcenac, Jerome Thibonnet
Summary: This study describes a method for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction. The reactivity of indole derivatives with iodine at position 3 was studied using various cross-coupling reactions. Sonogashira, Suzuki-Miyaura, Stille, and Heck cross-couplings provided a variety of di-, tri- and tetra-substituted indole-2-carbonitriles.
Article
Chemistry, Organic
Sushree Ranjan Sahoo, Biswajit Das, Debayan Sarkar, Hans Reuter
Summary: A temperature-controlled synthesis of multi-substituted 4-alkynyl/trans 4-alkenyl coumarins was achieved using a metal salt cascade approach. Water served as both a nucleophile and a hydrogen source, while the presence of a metal salt facilitated the reduction of alkyne. This method overcomes the structural shortcomings of existing Sonogashira and Heck coupling reactions. Furthermore, the obtained 2,3-disubstituted coumarins can be easily converted into 2,3-disubstituted dihydrocoumarins, which are important building blocks in organic transformations.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Editorial Material
Chemistry, Multidisciplinary
Soji Shimizu
Summary: Porphyrin analogues have attracted intensive investigations due to their rich coordination chemistry and unique optical and electrochemical properties. Among them, subporphyrins, especially the boron-free ones, have long been awaited. Recently, Kim, Osuka, and Song successfully synthesized a boron-free subporphyrin by introducing an exocyclic double bond at the meso-position and subsequent reduction to obtain macrocyclic conjugation. This seminal work will significantly facilitate studies on coordination chemistry and applications in materials science, as the availability of free base porphyrins is crucial for the development of porphyrin chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Hidehisa Kawashima, Narihito Ogawa, Ryohei Saeki, Yuichi Kobayashi
CHEMICAL COMMUNICATIONS
(2016)
Article
Chemistry, Organic
Yuichi Kobayashi, Masao Morita, Narihito Ogawa, Daiki Kondo, Toshifumi Tojo
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Organic
Atsushi Ikoma, Narihito Ogawa, Daiki Kondo, Hiroki Kawada, Yuichi Kobayashi
Article
Chemistry, Organic
Kyohei Wada, Masahiro Sakai, Hidehisa Kawashima, Narihito Ogawa, Yuichi Kobayashi
Article
Chemistry, Organic
Narihito Ogawa, Takuo Sugiyama, Masao Morita, Yuta Suganuma, Yuichi Kobayashi
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Narihito Ogawa, Yuichi Kobayashi
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2017)
Article
Chemistry, Organic
Yasutaka Shimotori, Masayuki Hoshi, Mari Murata, Narihito Ogawa, Tetsuo Miyakoshi, Taisei Kanamoto
HETEROCYCLIC COMMUNICATIONS
(2018)
Article
Multidisciplinary Sciences
Yu Sawada, Tetsuya Honda, Satoshi Nakamizo, Atsushi Otsuka, Narihito Ogawa, Yuichi Kobayashi, Motonobu Nakamura, Kenji Kabashima
SCIENTIFIC REPORTS
(2018)
Article
Chemistry, Organic
Riku Shinohara, Narihito Ogawa, Hidehisa Kawashima, Kyohei Wada, Shun Saito, Takashi Yamazaki, Yuichi Kobayashi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Shun Hirasawa, Ken Mukai, Shinnosuke Sakai, Shinnosuke Wakamori, Takahiro Hasegawa, Kazunori Souma, Nobuhiro Kanomata, Narihito Ogawa, Mamoru Aizawa, Makoto Emoto
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Riku Shinohara, Hidehisa Kawashima, Narihito Ogawa, Yuichi Kobayashi
Article
Chemistry, Organic
Riku Shinohara, Masao Morita, Narihito Ogawa, Yuichi Kobayashi
Article
Chemistry, Organic
Narihito Ogawa, Ryoya Imaizumi
Article
Chemistry, Organic
Yasutaka Shimotori, Masayuki Hoshi, Narihito Ogawa, Tetsuo Miyakoshi, Taisei Kanamoto
HETEROCYCLIC COMMUNICATIONS
(2020)
Article
Chemistry, Organic
Narihito Ogawa, Shinsaku Sone, Song Hong, Yan Lu, Yuichi Kobayashi
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
