Article
Chemistry, Multidisciplinary
Roberto Serrano, Yaroslav D. Boyko, Lucas W. Hernandez, Aleksandras Lotuzas, David Sarlah
Summary: The concise total syntheses of oxidized norcembranoid terpenoids (-)-scabrolide A and (-)-yonarolide have been achieved in 10 and 11 steps, respectively, by integrating two chiral-pool-derived fragments, including a [5,5]-bicyclic lactone accessed through a powerful Ni-catalyzed pentannulation of functionalized cyclopentenone with methylenecyclopropane and subsequent fragmentation. Additional features included a Liebeskind-Srogl coupling, induction of a cyclization/elimination cascade by a zinc-amido base, and installation of a sensitive enedione motif by latestage ?-oxidation.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Xinpei Cai, Lei Li, Ye-Cheng Wang, Jianhan Zhou, Mingji Dai
Summary: In this paper, we describe the complete synthesis of phleghenrines A and C from commercially available starting materials in 7 and 8 steps, respectively. Key steps include an inverse electron-demand Diels-Alder reaction between a masked o-benzoquinone and a N-protected enamine to generate a bicyclo[2.2.2]octenone core, a Bu''chner-Curtius-Schlotterbeck one-carbon insertion to expand the bicyclo[2.2.2]octenone to a bicyclo[3.2.2]nonenone, and Trauner's modified 2-pyridone synthesis to install the 2-pyridone moiety.
Article
Chemistry, Organic
Yingjie Wang, Biao Yu
Summary: The total syntheses of two antiangiogenic anthraquinone glycosides, aturanosides A and B, were achieved in an expeditious manner, emphasizing anthraquinone synthesis, phenol glycosylation, alpha-D-glucosaminoside installation, and judicious use of protecting groups.
Article
Chemistry, Organic
Ming Wang, Ya Wu, Mei Xu, Sheng Liu
Summary: An efficient synthetic route to iheyamine A and its analogues was discovered, involving a crucial one-pot transformation that included C-C migration to form the characteristic seven-membered ring. Subsequent addition of acetone to iheyamine A initiated a cascade process to complete the total synthesis of iheyamine B.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ming Wang, Ya Wu, Mei Xu, Sheng Liu
Summary: An efficient synthetic route to iheyamine A and its analogues was discovered, involving a crucial one-pot transformation with C-C migration to form the characteristic seven-membered ring. The subsequent addition of acetone to iheyamine A initiated a cascade process leading to the complete total synthesis of iheyamine B.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hongchang Tian, Yinxia Wu, Xiujuan Li, Zhen Hao, Wenyan He, Xiangdi Huang, Wen Chen, Hongbin Zhang
Summary: In this article, we present the first total synthesis of Kopsaporine related alkaloids. Our structure-unit-based strategy utilizes intramolecular Pummerer rearrangement induced nucleophilic cyclization/aza-Prins cyclization to construct the hexahydrocarbazole skeleton, olefin migration vinylogous alkylation to establish the C20 all-carbon quaternary center, iridium complex mediated radical addition to fuse the aspidofractine framework, unprecedented IBX oxidation to introduce the alpha-hydroxyketone moiety, and bioinspired retro-Aldol/Aldol reaction to convert kopsaporine to kopsiloscine A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Bolin Chen, Yufen Yang, Xijing Zhang, Dongdong Xu, Yuanjun Sun, Yue Chen, Liang Wang
Summary: In this study, concise and divergent total syntheses of fusicoccane members brassicicenes A, R, and T were reported. The key feature of the synthesis is the rapid construction of the 5/8/5 tricyclic core via four steps, followed by concise oxidation state adjustment.
Article
Chemistry, Organic
Hesi Yang, Yan Zhang, Wei Chen, Hongliang Shi, Liang Huo, Jia Li, Huilin Li, Xingang Xie, Xuegong She
Summary: This article describes the first total syntheses of two novel ansamacrolactams, (+/-)-catellatolactams A and B, in 5 and 8 steps, respectively. The synthesis strategy involves an amidation reaction, a regioselective C-H insertion, and an RCM reaction to form the macrocycles with E-olefin. The concise and scalable synthesis provided over 200 mg of the target molecules.
Article
Chemistry, Multidisciplinary
Kaixiang Xu, Shan Mu, Huijuanzi Rao, Jialei Hu, Hanfeng Ding
Summary: The asymmetric total syntheses of (+)-vulgarisins A-E, which share a rare and highly oxygenated [5-6-4-5] tetracyclic core structure that were isolated from P. vulgaris Linn., have been described for the first time in a divergent manner. Key transformations include: 1) a catalytic asymmetric intramolecular cyclopropanation to forge the A ring bearing desired stereochemistry at C14; 2) a one-pot borylation/conjugate addition process for creation of the C1-C11 bond; 3) a Wolff ring contraction to assemble the bicyclo[3.2.0]heptane subunit (CD rings); and 4) a stereocontrolled pinacol cyclization for construction of the central B ring of the natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Taehwan Hwang, Joseph P. Tuccinardi, Alexandra A. Beard, Amy C. Jackson, Min J. Jung, John L. Wood
Summary: This article describes the first total syntheses of (+/-)-dracocephalone A (1) and (+/-)-dracocequinones A (4) and B (5). The synthesis was initially envisioned as proceeding through an intramolecular isobenzofuran Diels-Alder reaction but evolved into a Lewis acid-promoted spirocyclization. This highly diastereoselective transformation set the stage for the formation of trans-decalin and a late-stage Suarez oxidation, leading to the desired products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Zhanchao Meng, Alois Fuerstner
Summary: The marine natural product scabrolide A was synthesized by a series of chemical reactions, including rearrangement, ring closure, and epoxidation, to form the carbon backbone and the correct stereochemistry of the compound.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Haruka Fujino, Masanori Nagatomo, Masayuki Inoue
Summary: Hikizimycin is a potent anthelmintic and antibacterial natural product with a complex structure that has attracted synthetic chemists since its structural determination in the early 1970s. Efforts have culminated in synthetic approaches including the synthesis of protected hikosamines and total synthesis of Hikizimycin, showcasing the evolution of modern natural product synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Tomoya Mashiko, Yuta Shingai, Jun Sakai, Shinya Adachi, Akinobu Matsuzawa, Shogo Kamo, Kazuyuki Sugita
Summary: The total syntheses of (+)-ganocin A and (-)-cochlearol B, featuring pentacyclic skeletons, in optically active forms, were reported. Key steps such as asymmetric Corey-Bakshi-Shibata reduction, phenolic oxidative cyclization, intramolecular radical cyclization-benzylic oxidative cyclization sequence, and intramolecular [2 + 2] photocycloaddition were utilized, enabling enantioselective access with a longest linear sequence of 17 steps and 9% overall yield for (+)-ganocin A and with 16 steps and 9% overall yield for (-)-cohlearol B.
Article
Chemistry, Multidisciplinary
Raphael J. Zachmann, Kenzo Yahata, Mira Holzheimer, Maxime Jarret, Cornelia Wirtz, Alois Fuerstner
Summary: The structure of prorocentin has been revised through a flexible synthesis approach, showing that the previously proposed structure is incorrect. The new, more plausible structure was obtained using methods such as gold-catalyzed spirocyclization reactions. This study has important implications for the understanding of prorocentin's structure.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Joseph P. Tuccinardi, John L. Wood
Summary: This article describes the first total syntheses of the nor-furanocembranoid natural products (+)-ineleganolide and (-)-sinulochmodin C. The synthetic strategy is based on a transannular Michael reaction and a diastereoselective radical cyclization, and discusses the unexpected stereochemical nuances during the evolution and completion of the total synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Chu-En Chou, Yi-An Chen, Yi-Ching Lin, Shih-Chieh Kao, Chieh-Yu Chang, Yen-Ku Wu
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Mitsuhiro Ueda, Kazuya Kamikawa, Takahide Fukuyama, Yi-Ting Wang, Yen-Ku Wu, Ilhyong Ryu
Summary: A novel method has been developed for site-selective alkenylation of a broad variety of substrates, including sterically hindered acyclic and alicyclic substrates. This method allows for the generation of (E)-2-alkylvinylphenylsulfones in high yield by utilizing persulfate and 1,2-bis(phenylsulfonyl)ethene. The compact size of the sulfate radical employed in C-H activation and cleavage allows for the alkenylation of sterically hindered C-H bonds, broadening the scope of substrates that can be efficiently transformed.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Yin-Jia Jhang, Chieh-Yu Chang, Yu-Huan Lin, Chein-Chung Lee, Yen-Ku Wu
Summary: The presented method allows for the direct substitution of allylic alcohols with sodium arylsulfinates through the cooperative action of palladium catalysts, phenylboronic acid, and titanium tetraisopropoxide. This protocol was used to achieve a concise synthesis of bicalutamide, an anti-androgen compound for treating prostate cancer.
TETRAHEDRON LETTERS
(2021)
Review
Chemistry, Multidisciplinary
Yi-Ching Lin, Yen-Ku Wu
Summary: The review provides an overview of research efforts towards assembling the unique carboskeleton of Crinine and vittatine alkaloids, which have served as inspiration for the development of reaction methods since the 1950s.
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2021)
Article
Chemistry, Applied
Yi-Ting Wang, Yi-Lun Shih, Yen-Ku Wu, Ilhyong Ryu
Summary: Site-selective C(sp(3))-H alkenylation was achieved under photo-irradiation in the presence of a catalytic decatungstate anion. The reaction successfully combines radical addition/beta-scission sequence with photocatalytic C(sp(3))-H functionalization. The decatungstate anion participates in a chain-repairing step in reactions with weaker C-H bonds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Chieh-Yu Chang, Chun-Jen Chen, Sheng-Hao Huang, Shih-Chieh Kao, Yen-Ku Wu
Summary: A concise route to (+/-)-taiwaniaquinol B is described, in which the 6-5-6-fused ring system is constructed by sequencing a Fries rearrangement and a photo-Nazarov cyclization. The use of photoirradiation conditions is found to be crucial for promoting the key electrocyclization and mitigating the competing oxo-Michael pathway.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yi-Lun Shih, Sheng-Hao Huang, Yen-Ku Wu, Ilhyong Ryu
Summary: Photocatalytic C(sp(3))-H allylation, alkynylation, and imination using unsaturated benzenesulfonyl compounds were investigated with decatungstate W10O324- as the photocatalyst. In all these reactions, selective cleavage of C(sp(3))-H bonds was achieved and combined with the radical addition/ss-scission sequence.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2022)
Article
Chemistry, Multidisciplinary
Xin-Jie Lin, Shih-Peng Huang, Min-Jie Huang, Chien-Lung Wang, Chi-How Peng, Hsueh-Ju Liu, Yen-Ku Wu
Summary: This article describes our efforts in establishing a practical and sustainable synthesis of bis(2-hydroxy-3,5-di-t-butylphenyl)methanone. We found that the phenol-aldehyde condensation reaction can be efficiently catalyzed by sulfonic acid-functionalized microporous carbon spheres (MCS-SO3H). Additionally, we developed practical and sustainable procedures for the synthesis of the title ligand by using readily available reagents instead of toxic chromium trioxide and fuming boron tribromide.
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Yi-Lun Shih, Yen-Ku Wu, Mamoru Hyodo, Ilhyong Ryu
Summary: A catalytic amount of decatungstate photocatalyst under black light irradiation was able to promote the oxidative cleavage of C=C bonds with molecular oxygen, resulting in the formation of both aromatic and aliphatic ketones. The use of a high-power ultraviolet light-emitting diode at 365 nm for the continuous flow reaction of alpha-methylstyrene significantly reduced the reaction time.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Chen-Yang Tsai, Yin-Jia Jhang, Yen-Ku Wu, Ilhyong Ryu
Summary: This study reports a protocol for alkene hydroxyalkenylation and a photocatalytic protocol for alkoxyalkenylation. Alkenes can be converted into the corresponding 1-phenylsulfonyl-4-hydroxyalkenes or alkoxyalkenes in good to high yields using a persulfate anion as an oxidation reagent and 1,2-bis(phenylsulfonyl)ethylene as a radical acceptor. The methods exhibit wide substrate adaptability and regioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Zih-Siang Hong, Shih-Chieh Kao, Yu-Tsen Cheng, Chun-Jen Chen, Yen-Ku Wu
Summary: In this study, a photoflow method was developed for the radical-based coupling of unactivated arenes and aryl chlorides. The reaction proceeded smoothly at ambient temperature without the need for metal catalysts. Importantly, the reaction conditions were optimized for chloroarenes with different electronic properties. Despite the generally lower reactivity of aryl chlorides compared to their iodide and bromide counterparts, the developed protocol efficiently converted readily available and inexpensive chloroarenes into unsymmetrical biaryl products.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Wan-Ling Peng, Yin-Jia Jhang, Chieh-Yu Chang, Po-Kai Peng, Wei-Ting Zhao, Yen-Ku Wu
Summary: A total synthesis of racemic mersicarpine from diethyl 4-oxopimelate is described, utilizing a 2-indolyl radical cyclization to construct the pyrido[1,2-a]indole scaffold with an all-carbon quaternary stereocenter.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yi-Ching Lin, Ko-Wang Yen, Hsuan-Jen Lin, Yi-Chi Yang, Yen-Ku Wu
Summary: This study presents a method for synthesizing diaryl cyclic vinylogous esters, where the site selectivity of the second arylation is modulated by the substitution pattern of the substrates during a programmed sequence of C(sp(3))-H arylation events. The optimized reaction system effectively prevents the formation of dihomo-arylated products.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Chia-Chen Chien, Shih-Chieh Kao, Chun-Jen Chen, Yen-Ku Wu
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Organic
Hsin-Ju Huang, Yi-Ting Wang, Yen-Ku Wu, Ilhyong Ryu
ORGANIC CHEMISTRY FRONTIERS
(2020)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
