Review
Chemistry, Applied
Nengzhong Wang, Xiao Xiao, Cheng-Xiong Liu, Hui Yao, Nianyu Huang, Kun Zou
Summary: This review discusses the synthesis of tetracyclic pyridocarbazoles, focusing on different approaches for establishing the all-carbon quaternary center at C5. Classic synthetic reactions, palladium-catalyzed asymmetric decarboxylative allylation reactions, and thiourea-catalyzed asymmetric Michael addition reactions have been employed. Late-stage key transformations in the total syntheses of aspidosperma and kopsia alkaloids are also described.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Wesley J. Olivier, Alex C. Bissember, Jason A. Smith
Summary: The total syntheses of Stemona alkaloids sessilifoliamides B and D, as well as the second synthesis of sessilifoliamide C, were successfully completed from a simple pyrrole substrate. The bicyclic lactam core was prepared on a gram scale via a Bronsted acid mediated cyclization and controlled oxidation with Dess-Martin periodinane. Yield percentages for the synthesis of sessilifoliamides B, C, and D were 24%, 13%, and 17% respectively, over multiple steps.
Article
Chemistry, Organic
Giovanni Bernardi Rosso, Bruno Matos Paz, Ronaldo Aloise Pilli
Summary: The proposed structure for the putative Stemona alkaloid named parvistemoamide has been questioned. The study also reports on the intramolecular Friedel-Crafts alkylation of a furan molecule, leading to the synthesis of related compounds.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Cheng Zhu, Jianbo Jin, Mengyu Gao, Maria C. Folgueras, Ye Zhang, Chung-Kuan Lin, Peidong Yang, Alexander M. Oddo
Summary: The structural diversity and tunable optoelectronic properties of halide perovskites come from the rich chemistry of metal halide ionic octahedra. The ability to manipulate the assembly of these octahedral building blocks is crucial for constructing new perovskite materials.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Dorian Didier, Felix Reiners
Summary: Strained ring systems have become increasingly important in natural product syntheses and drug discovery programs in recent years. Our work focuses on the construction and functionalization of unsaturated four-membered carbo- and heterocycles, as well as their applications in further reactions.
Article
Chemistry, Multidisciplinary
Sujenth Kirupakaran, Glib Arago, Christoph Hirschhaeuser
Summary: A synthetic strategy for all aldohexoses with individually addressable protecting groups from dihalomethane C-1-units is reported. The underlying synthesis of C-6-sugar alcohols relies on three consecutive Matteson sequences, vinylation and bishydroxylation. Erythro and threo isomers have been realized for every glycol motif by strategic variation of the sequence.
Article
Chemistry, Multidisciplinary
Sujenth Kirupakaran, Glib Arago, Christoph Hirschhauser
Summary: This article presents a synthetic strategy for all aldohexoses with individually addressable protecting groups from dihalomethane C-1-units. The synthesis of C-6-sugar alcohols relies on three consecutive Matteson sequences, vinylation and bishydroxylation. Erythro and threo isomers have been achieved for every glycol motif by strategic variation of the sequence.
Article
Chemistry, Multidisciplinary
Feifei He, Shangbiao Feng, Yulong Zhao, Hongliang Shi, Xiaoguang Duan, Huilin Li, Xingang Xie, Xuegong She
Summary: A gold-catalyzed reaction is developed to access tricyclic cores using the commonly shared bicyclic decahydroquinoline motif. These cores are then used for the divergent total syntheses of five Lycopodium alkaloids in a concise manner. Key transformations include ring cyclization, hydration, fragmentation, and construction of specific motifs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Zhihua Cheng, Matthew R. Jones
Summary: The study reports the self-assembly of 2D chiral superlattices from achiral tetrahedron-shaped building blocks, explains the formation mechanism, and lays the scientific foundation for the high-throughput assembly of planar chiral metamaterials.
NATURE COMMUNICATIONS
(2022)
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.
Review
Chemistry, Physical
Qianwei Liu, Bixin Jin, Qin Li, Huanzhi Yang, Yunjun Luo, Xiaoyu Li
Summary: Self-assembly is a common phenomenon in living systems, and scientists have been trying to emulate its intricacy, homogeneity, and versatility in artificial building blocks. Self-sorting assembly in multicomponent systems allows for the spontaneous recognition and spatial aggregation of the same or interactive building units, leading to well-ordered products or hierarchical structures in a one-step manner. This efficient assembly strategy has attracted significant research attention, particularly in artificial systems using supramolecular and polymeric building blocks.
Article
Polymer Science
Ying Wang, Yanni Xia, Zhengjiang Hua, Chengjian Zhang, Xinghong Zhang
Summary: This work presents the copolymerization of propylene carbonate with carbonyl sulfide to prepare poly(thioether)s, which provides a new approach for the application of cyclic carbonates and the synthesis of thioether-based polymers.
Article
Multidisciplinary Sciences
Zaiwang Zhao, Yujuan Zhao, Runfeng Lin, Yuzhu Ma, Lipeng Wang, Liangliang Liu, Kun Lan, Jie Zhang, Hanxing Chen, Mengli Liu, Fanxing Bu, Pengfei Zhang, Liang Peng, Xingmiao Zhang, Yupu Liu, Chin-Te Hung, Angang Dong, Wei Li, Dongyuan Zhao
Summary: We report on the fabrication of three-dimensional hierarchical core-satellite SiO2@monomicelle spherical superstructures through a previously unexplored monomicelle interfacial super-assembly route. The ultrathin single layer of monomicelle subunits with hexagon-like regular discontinuous distribution on solid spherical interfaces can be achieved, and the number of monomicelles on colloidal SiO2 interfaces can be quantitatively controlled. This strategy provides a controllable way for building multiscale hierarchical regular micro- and/or macroscale materials and devices.
Article
Chemistry, Organic
Qixia Bai, Ying Liu, Tun Wu, Haoyue Su, Gang Chen, Yuming Guan, Ming Wang, Ting-Zheng Xie, Zhe Zhang, Pingshan Wang
Summary: The structures of metallocages are sensitive to various stimuli due to the dynamic reversibility of the coordination-driven force, with the strength of the metal ligand dative bonds playing a crucial role.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Jacques Renault, Christelle Bouvry, Jean-Francois Cupif, Jean-Pierre Hurvois
Summary: The syntheses of several alkaloids and nitrogen-containing compounds were described in this study, including N-Boc-coniine (14b), pyrrolizidine (1), 6-coniceine (2), and pyrrolo[1,2a]azepine (3). New C-C bonds in the alpha position relative to the nitrogen atom were formed through alkylation reactions. The pyrrolidine ring was formed in an aqueous medium, while the azepane ring was efficiently formed in N,N-dimethylformamide (DMF) as the solvent, using a 7-exo-tet cyclization process.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
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, 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
Plant Sciences
Akihiro Ochi, Makoto Yoritate, Tomofumi Miyamoto, Kazuteru Usui, Gorawit Yusakul, Waraporn Putalun, Hiroyuki Tanaka, Go Hirai, Satoshi Morimoto, Seiichi Sakamoto
Summary: Harringtonine (HT), derived from Cephalotaxus species, displays potent antiproliferative activity against myeloid leukemia cells. By replacing the C-5' methyl group with different hydrocarbon chains, the derivative 1f showed the highest cytotoxicity among the HT ester derivatives produced, exhibiting strong antiproliferative activity against HL-60 and HeLa cells.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Biochemistry & Molecular Biology
Yui Fujii, Makoto Yoritate, Kana Makino, Kazunobu Igawa, Daiki Takeda, Daiki Doiuchi, Katsuhiko Tomooka, Tatsuya Uchida, Go Hirai
Summary: Seven mono- and dihydroxycholesterols were synthesized by direct C-H oxidation of the cholestane skeleton using a Ru(Bpga) catalyst, which showed high selectivity for tertiary C-H. The reaction yielded a mixture of 25-, 20-, 17-, and 14-oxygenated cholesterols that could be easily separated by high-performance liquid chromatography. This suggests that late-stage C-H oxidation could be a viable strategy for preparing candidate metabolites of biologically important molecules.
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
Yasuki Soda, Yasukazu Sugiyama, Shunsei Sato, Kana Shibuya, Junya Saegusa, Tomoe Matagawa, Sayaka Kawano, Makoto Yoritate, Keisuke Fukaya, Daisuke Urabe, Takeshi Oishi, Kento Mori, Siro Simizu, Noritaka Chida, Takaaki Sato
Summary: A stereodivergent method for the synthesis of totally substituted butenolide and the synthesis of a series of stemoamide-type alkaloids with good anti-inflammatory activity and low cytotoxicity have been reported in this study.
SYNTHESIS-STUTTGART
(2023)
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
Chemistry, Multidisciplinary
Taishi Miura, Makoto Yoritate, Go Hirai
Summary: In this study, a protection-group-free and photoredox-catalyzed C-glycosylation method using glycosyl sulfinates and Michael acceptors via the Giese radical addition is reported. This method provides a useful tool for synthesizing C-glycoside analogs of naturally occurring glycoconjugates in chemical biology studies.
CHEMICAL COMMUNICATIONS
(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)
