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
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)
Article
Chemistry, Organic
Patrick Swieca, Peter Spiteller
Summary: In this study, an efficient and short total synthesis method of bulgarein (1), a natural compound with cytotoxic activity in Bulgaria inquinans, was reported. The key steps in the synthesis include a SUZUKI-MIYAURA coupling reaction of two substituted naphthalene derivatives and a polyphosphoric acid (PPA) mediated condensation reaction to form the benzo[j]fluoranthene skeleton. Bulgarein (1) was synthesized in 4 steps with an overall yield of 25%.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
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
Chemistry, Applied
Laura Stief, Andreas Speicher
Summary: A polyprenyl side chain was introduced into the heterocyclic quinoline moiety through Suzuki-Miyaura coupling, enabling the synthesis of Aurachin B from Stigmatella aurantiaca. This prenylated quinoline could then be transformed into the related compound Aurachin A through an epoxidation-ring opening cascade.
ADVANCED SYNTHESIS & CATALYSIS
(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
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.
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, 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)
Article
Chemistry, Organic
Yuichiro Kawamoto, Toyoharu Kobayashi, Hisanaka Ito
Summary: Stachyodin A, with a unique spirotetrahydrofuran ring system, was isolated from the roots of Indigofera stachyodes in 2018. The first total synthesis of racemic stachyodin A was accomplished in 14 steps.
Article
Chemistry, Multidisciplinary
Hamed M. Alshammari, Obaid F. Aldosari, Mohammad Hayal Alotaibi, Raja L. Alotaibi, Mosaed S. Alhumaimess, Moataz H. Morad, Syed Farooq Adil, Mohammed Rafi Shaik, Mohammad Shahidul Islam, Mujeeb Khan, Abdulrahman Alwarthan
Summary: Pd/C catalysts on activated carbon with varying palladium content showed high catalytic activity for Suzuki-Miyaura coupling reactions and Mizoroki-Heck cross-coupling reactions. The catalyst with 3% Pd/C demonstrated better efficiency and reusability compared to other synthesized catalysts, indicating the significance of high 'Pd' content and uniform impregnation on the catalyst activity.
APPLIED SCIENCES-BASEL
(2021)
Article
Chemistry, Organic
Moemi Kanto, Makoto Sasaki
Article
Chemistry, Organic
Hirofumi Yamamoto, Maho Ueda, Naoto Yamasaki, Akiyoshi Fujii, Ikuo Sasaki, Kazunobu Igawa, Yusuke Kasai, Hiroshi Imagawa, Mugio Nishizawa
Article
Chemistry, Organic
Kotaro Iwasaki, Satori Sasaki, Yusuke Kasai, Yuki Kawashima, Shohei Sasaki, Takanori Ito, Mari Yotsu-Yamashita, Makoto Sasaki
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Naoto Yamasaki, Marina Kanno, Kyohei Sakamoto, Yusuke Kasai, Hiroshi Imagawa, Hirofumi Yamamoto
Article
Chemistry, Multidisciplinary
Keisuke Sakurai, Makoto Sasaki, Haruhiko Fuwa
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Organic
Makoto Sasaki, Kotaro Iwasaki, Keisuke Arai
Article
Chemistry, Organic
Hirofumi Yamamoto, Yuichi Takagi, Naoto Yamasaki, Tadashi Mitsuyama, Yusuke Kasai, Hiroshi Imagawa, Yutaro Kinoshita, Naohiro Oka, Masanori Hiraoka
Article
Chemistry, Medicinal
Maichi Hama, Abdelsamed Elshamy, Tatsuro Yoneyama, Yusuke Kasai, Hirohumi Yamamoto, Kana Tanigawa, Ayari Oshiro, Masaaki Noji, Sayaka Ban, Hiroshi Imagawa, Akemi Umeyama
Article
Chemistry, Medicinal
Tsuyoshi Yanagimoto, Suguru Kishimoto, Yusuke Kasai, Nobuaki Matsui, Miwa Kubo, Hirofumi Yamamoto, Yoshiyasu Fukuyama, Hiroshi Imagawa
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2020)
Article
Chemistry, Organic
Tsuyoshi Yanagimoto, Sayo Yamada, Yusuke Kasai, Hirofumi Yamamoto, Miwa Kubo, Yoshiyasu Fukuyama, Hiroshi Imagawa
Summary: Naturally occurring (+)-spirotenuipesines A and B can promote the biosynthesis of neurotrophic factors and potentially serve as promising drugs for treating neurodegenerative diseases. By synthesizing the racemic compound, differentiation-inducing activity against PC12 cells was observed in a cell culture medium.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Medicinal
Yusuke Kasai, Takamitsu Ogawa, Mao Kawata, Kana Tanigawa, Abdelsamed I. Elshamy, Tatsuro Yoneyama, Masaaki Noji, Akemi Umeyama, Hiroshi Imagawa
Summary: The ortho-tyrosinol derivative, a key synthetic intermediate for alkaloidal metabolites of Cordyceps, was synthesized from L-phenylalanine methyl ester through condensation with crotonic acid and oxidative intramolecular lactone formation. Subsequent elongation of the side chain involving a cross-metathesis reaction and deprotection resulted in the efficient synthesis of cordytakaoamide B and cordycepamide C in a few steps. The S-configurations at the C-2 position of both cordytakaoamide B and cordycepamide C were confirmed by comparing their optical rotation with synthetic samples.
NATURAL PRODUCT COMMUNICATIONS
(2022)
Article
Biotechnology & Applied Microbiology
Tatsuro Yoneyama, Abdelsamed Elshamy, Junpei Yamada, Walaa A. El-Kashak, Yusuke Kasai, Hiroshi Imagawa, Sayaka Ban, Masaaki Noji, Akemi Umeyama
Summary: Cordyceps spp. is a widely recognized healthy food with traditional uses and bio-functionalities. Chemical characterization of an entomopathogenic fungus extract led to the identification of two new metabolites and four known metabolites. One of the metabolites exhibited antimicrobial activity and significant binding affinities to specific proteins.
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
(2022)
Article
Chemistry, Organic
Shota Yanagi, Tomoya Sugai, Takuma Noguchi, Masato Kawakami, Makoto Sasaki, Shinsuke Niwa, Asako Sugimoto, Haruhiko Fuwa
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
Article
Biochemistry & Molecular Biology
Eva Alonso, Andres C. Vieira, Ines Rodriguez, Rebeca Alvarino, Sandra Gegunde, Haruhiko Fuwa, Yuto Suga, Makoto Sasaki, Amparo Alfonso, Jose Manuel Cifuentes, Luis M. Botana
ACS CHEMICAL NEUROSCIENCE
(2017)