Article
Chemistry, Organic
Abudulajiang Nasier, Xihao Chang, Chang Guo
Summary: An efficient and valuable N-N dimerization reaction of N-alkoxyamides is reported under undivided electrolytic conditions. A crucial role is played by an N-centered radical generated from the cleavage of the N-H bond under electrolytic conditions. Various N-alkoxyamides bearing different substituents are suitable in this transformation, furnishing the corresponding hydrazines in up to 92% yield.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Sushant Bhalerao, Hemchandra Chaudhari
Summary: An efficient and fast method for synthesizing esters from N-alkoxyamides has been reported using easily available N-Chloro-N-(phenylsulfonyl)benzenesulfonamide (NCBSI). This metal and ligand-free protocol occurs under mild reaction conditions and can incorporate a wide variety of amides, leading to the formation of functionalized esters with high yields, highlighting its versatility and chemoselectivity.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Organic
Sung June Kim, Sunhee Lee, Ikyon Kim
Summary: In this study, the expansion of nitrogen-fused heteroaromatic chemical space, such as indolizine and pyrrolo[1,2-a]pyrazine, was achieved through FeCl3-catalyzed nucleophilic addition of these compounds to a wide range of azolinium systems, resulting in novel N-fused heteroaromatic scaffolds with regioselective dearomatized N-heterocyclic substituents. Nucleophilic addition of indolizines and pyrrolo[1,2-a]pyrazines mainly occurred at the C1 position of isoquinoliniums and at the C4 site of quinoliniums.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Zhi-Yuan Zhao, Ming Cui, Elisabeth Irran, Martin Oestreich
Summary: This study successfully achieved highly enantioselective silylation of 3-substituted 2H-azirines using a copper-catalyzed reaction with a silyl boronic ester as a latent silicon nucleophile. The resulting C-silylated, unprotected (N-H) aziridines were obtained in high yields and with excellent enantioselectivities, and they can be further converted into valuable compounds without significant loss of enantiomeric excess.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Shinichiro Fuse, Sena Kanda, Hisashi Masui
Summary: Valuable indole derivatives were synthesized via the sequential 1,2-addition/nucleophilic substitution of indolyl-3-carbaldehydes. Microflow technology was used to suppress undesired reactions caused by unstable intermediates, leading to higher yields and reproducibility. The study provides a rapid and efficient method for the synthesis of structurally diverse indole derivatives.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Mengsi Zhang, Hailong Ma, Baojun Li, Ke Sun, Haotian Lu, Wenbo Wang, Xiaoyu Cheng, Xiaoxuan Li, Yun Ding, Aiguo Hu
Summary: This study investigated the reactivity of diradical/zwitterion dichotomy and the thermally induced sigma,pi-diradicals with the use of experimental and computational methods. The research demonstrated the transformation from open-shell diradicals to closed-shell zwitterions during the addition process, with a notable nonplanar geometry essential for symmetry-breaking action. The results provided insight into the intriguing biological activity and unique mechanistic actions involved in diradical chemistry.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Alexey V. Nelyubin, Nikita A. Selivanov, Alexander Yu. Bykov, Ilya N. Klyukin, Alexander S. Novikov, Andrey P. Zhdanov, Natalia Yu. Karpechenko, Mikhail S. Grigoriev, Konstantin Yu. Zhizhin, Nikolay T. Kuznetsov
Summary: In this study, a convenient and straightforward approach to the preparation of borylated amidines based on the closo-dodecaborate anion was developed in two stages. The method features simple chemical apparatus, mild conditions, and high yields of final products.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Chemistry, Organic
Bastian Jakob, Ichraf Slimani, Andreas Diehl, Naceur Hamdi, Georg Manolikakes
Summary: This study presents a palladium-catalyzed decarboxylative 1,2-addition of carboxylic acids to glyoxylic acid esters, providing access to the mandelic acid scaffold in good yields. The method utilizes readily available benzoic acids as a more sustainable alternative to preformed organometallic nucleophiles, showing promise for environmentally friendly organic synthesis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yuan Zhang, Han Luo, Qixing Lu, Qiaoyu An, You Li, Shanshan Li, Zongyuan Tang, Baosheng Li
Summary: The study focused on cascade nucleophilic addition reactions of 1,2,3-triazines with activated acetonitriles or ketones to construct highly substituted pyridines, addressing structural diversity issues in medicinal chemistry. The resulting pyridines serve as convenient precursors for the synthesis of related pharmaceuticals, and have been successfully applied in the synthesis of diverse biologically important molecules.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Norihiko Takeda, Yukiko Kobori, Motohiro Yasui, Yuki Matsumoto, Kotomi Orihara, Yusaku Kido, Masafumi Ueda
Summary: A new method for synthesizing 2-acyl pyrrolidines has been developed through sequential nucleophilic addition/ring contraction of alpha-bromo N-iminolactam with organometallic reagents. This reaction allows the incorporation of various groups, including aryl, heteroaryl, alkenyl, alkynyl, and alkyl groups, into the facial construction of 2-acyl pyrrolidines. Moreover, the 2-acyl pyrrolidine products can be further transformed into different compounds such as pyrrolidinyl alcohol, epoxide, b-lactam, and pyrazole.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Stephen A. Glover
Summary: This account describes the origins of research on the mutagenicity of N-acyloxy-N-alkoxyamides. The study focuses on their ability to mutate DNA in the Ames reverse mutation assay without the need for metabolic activation. The impact of structural variation on cellular access to, binding to, and reactivity with DNA is explored, with emphasis on hydrophobicity, electrophilic reactivity, steric effects, and intercalation.
AUSTRALIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Keisuke Fukaya, Takaaki Sato, Noritaka Chida, Daisuke Urabe
Summary: This study provides important insights into the theoretical analysis of complex molecular reactions by investigating the conformations and stereoselectivity of transition states. The findings reveal that the double-bond geometry and stereochemical configuration influence the conformations of the transition states, and that the CH-O hydrogen bond and CH-p interaction play critical roles in asymmetric induction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Masnun Naher, Chuyi Su, Jeffrey R. Harmer, Craig M. Williams, Paul V. Bernhardt
Summary: The utility and scope of Cu-catalyzed halogen atom transfer chemistry have been exploited in a variety of fields. This study demonstrates the ability to modulate the reactivity of the Cu catalyst using electrochemistry, resulting in unprecedented rate acceleration in Cu-catalyzed bulk electrosynthesis.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Changjin Son, Taegun Park, Sangwoo Lim
Summary: By adding ionic compounds and carboxylic acids to superheated water, the etching of Si3N4 without the use of H3PO4 and HF was demonstrated, reducing potential environmental and safety issues associated with conventional Si3N4 etching.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Organic
Haruki Ohno, Ryosuke Takahashi, Takuya Suga, Takahiro Soeta, Yutaka Ukaji
Summary: C,N-cyclic-N'-acyl azomethine imines with isoquinoline skeletons were investigated for their reactivity with diazo compounds via two different pathways. During the reaction with ethyl diazoacetate, an a-diazoacetate moiety was introduced at the C1-position of the resulting tetrahydroisoquinolines. Alternatively, diazomethane or trimethylsilyldiazomethane was used to synthesize 3-benzazepine derivatives via ring expansion.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yuya Okuyama, Mayu Kidena, Erina Kato, Sayaka Kawano, Koki Ishii, Kenta Maie, Kazuki Miura, Siro Simizu, Takaaki Sato, Noritaka Chida
Summary: A concise synthetic route to peracetylated all-nitrogenated sugars (ANSs) in seven steps from commercially available monosaccharides has been developed. The key to success is the use of sequential Overman rearrangement for ANS synthesis, which shows cytotoxicity against human cancer cell lines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Kazuki Miura, Sayaka Kawano, Takahiro Suto, Takaaki Sato, Noritaka Chida, Siro Simizu
Summary: The study found that madangamine A has strong anti-proliferative activity against human cancer cell lines by inhibiting lysosome function.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Seiya Katahara, Yasukazu Sugiyama, Mina Yamane, Yukinori Komiya, Takaaki Sato, Noritaka Chida
Summary: A five-step total synthesis of (+/-)-aspidospermidine based on a lactam strategy is reported, featuring an iridium-catalyzed reductive Michael addition/[3+2] cycloaddition cascade for the generation of a tricyclic ketone intermediate from a simple lactam. This strategy allows for easily available lactams to be used as stable surrogates of multisubstituted amines and could be applicable to a unified total synthesis of complex Aspidosperma alkaloids.
Article
Chemistry, Organic
Ryo Minamikawa, Keisuke Fukaya, Akihiro Kobayashi, Yukinori Komiyaa, Shio Yamamoto, Daisuke Urabe, Noritaka Chida, Takaaki Sato
Summary: The asymmetric total synthesis of fasicularin was achieved using a chiral N-alkoxyamide strategy, which changed the reactivity of the amide by incorporating a chiral alkoxy group onto an amide nitrogen. DFT calculations highlighted the importance of pyramidalization of the N-alkoxyamide nitrogen for the aza-spirocyclization reaction. The chiral alkoxy group was also utilized for stereocontrol to establish consecutive stereocenters with high diaste-reoselectivity in the iridium-catalyzed reductive Strecker reaction.
SYNTHESIS-STUTTGART
(2021)
Review
Chemistry, Organic
Takaaki Sato, Takahiro Suto, Yoshiyuki Nagashima, Shori Mukai, Noritaka Chida
Summary: Skipped dienes, found in various biologically active natural products, have relatively undeveloped synthesis methods compared to conjugated dienes due to challenges posed by the sp(3)-hybridized carbon between two olefins. Recent advances in the synthesis of skipped dienes for total synthesis of complex natural products are classified into three categories, focusing on methods to achieve both high stereoselectivity and convergency.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yasukazu Sugiyama, Yasuki Soda, Makoto Yoritate, Hayato Tajima, Yoshito Takahashi, Kana Shibuya, Chisato Ogihara, Takashi Yokoyama, Takeshi Oishi, Takaaki Sato, Noritaka Chida
Summary: In this article, the concise total synthesis of complex alkaloids using a lactam strategy is reported. The strategy enables the assembly of five-membered rings and the synthesis of tricyclic, tetracyclic and pentacyclic stemoamide-type alkaloids. The developed conditions for the lactam-selective nucleophilic reactions are highly versatile and applicable to the synthesis of different types of alkaloids.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2022)
Article
Chemistry, Organic
Shota Iiyama, Keisuke Fukaya, Yu Yamaguchi, Ami Watanabe, Hiroaki Yamamoto, Shota Mochizuki, Ryosuke Saio, Takashi Noguchi, Takeshi Oishi, Takaaki Sato, Noritaka Chida
Summary: The total synthesis of paclitaxel is achieved through a double Rubottom oxidation of the bis(silyl enol ether) derived from a tricarbocyclic diketone, efficiently installing a bridgehead olefin and C-5/C-13 hydroxy groups in one step. Additionally, a novel Ag-promoted oxetane formation method is used to smoothly construct the tetracyclic framework of paclitaxel.
Article
Materials Science, Multidisciplinary
Tomoka Yoshii, Mai Mochida, Kogi Kaizu, Yasuki Soda, Kazuyoshi Kanamori, Kazuki Nakanishi, Takaaki Sato, Hiroaki Imai, Daniel Citterio, Yuki Hiruta
Summary: In this study, an alkali-stable column packing material for reversed-phase preparative high-performance liquid chromatography (HPLC) was developed based on eggshells. The material showed excellent separation and stability in HPLC columns after surface treatment and modification.
ACS APPLIED POLYMER MATERIALS
(2022)
Article
Chemistry, Organic
Shona Banjo, Keisuke Nakata, Eiko Nakasuji, Soichiro Yasui, Noritaka Chida, Takaaki Sato
Summary: This study reports a copper-catalyzed electrophilic enamidation starting from alkynes. Hydrozirconation of an alkyne with the Schwartz reagent forms a vinyl zirconium intermediate, which undergoes a copper-catalyzed electrophilic enamidation with dioxazolones. The high functional group tolerance of hydrozirconation enables the use of functionalized alkynes, including esters. The developed conditions are successfully applied to synthesize partial structures found in biologically active natural products.
Article
Chemistry, Organic
Ayaha Kage, Yuya Okuyama, Erina Kato, Tomoe Matagawa, Sayaka Kawano, Siro Simizu, Noritaka Chida, Toshitaka Okamura, Takaaki Sato
Summary: Saponins have various biological and pharmacological activities, with the sugar moiety playing a crucial role in bioactivity. This report focuses on the synthesis and evaluation of saponins with all-nitrogenated sugar (ANS), where all oxygen atoms are replaced with nitrogen atoms. ANS glycosides of OSW-1 derivative, cholesterol, and diosgenin are synthesized through glycosylation with ANS in the presence of TMSOTf. The OSW-1 mimic with ANS exhibits significant cytotoxic activity (IC50 = 7.31 μM) and induces apoptosis.
Article
Chemistry, Organic
Keisuke Fukaya, Takaaki Sato, Noritaka Chida, Daisuke Urabe
Summary: This study provides important insights into the theoretical analysis of complex molecular reactions by investigating the conformations and stereoselectivity of transition states. The findings reveal that the double-bond geometry and stereochemical configuration influence the conformations of the transition states, and that the CH-O hydrogen bond and CH-p interaction play critical roles in asymmetric induction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Crystallography
Takeshi Oishi, Keisuke Fukaya, Takaaki Sato, Noritaka Chida
Summary: The title compound C29H36O9 features a fused tetracyclic system with complex molecular interactions. In the crystal, a three-dimensional network is constructed through hydrogen bonds and interactions, connecting molecules into helical chains along the c-axis direction. There is no valid C-H center dot center dot center dot pi interaction within the structure.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
(2021)
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)
