Article
Chemistry, Multidisciplinary
Liu-Peng Zhao, Peng-Juan Li, Lijia Wang, Yong Tang
Summary: A facile method for the construction of the aspidosperma core from indoles functionalized with a nonterminal N-allenamide and dimethyl methylenemalonate is described. The annulation reaction provides straightforward access to the tetracyclic spiroindoline skeleton with substituents at the C5 position occurring in many natural products. As an application of this reaction, the total synthesis of three important natural products was possible in short routes from tryptamine.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Zhengdong Yao, Huangdi Feng, Hui Xi, Chuanjun Xi, Weiping Liu
Summary: A novel dearomatization process was demonstrated for the production of fused polycyclic indolines via a CF3SO3H-mediated cascade ring-opening of a beta-lactam and hydroaminative cyclization. This method provides a new strategy for synthesizing important polycyclic indoline-2-amine derivatives with moderate to excellent yields and good functional group tolerance. Furthermore, transformation of the product can smoothly deliver the corresponding acid, alcohol, and amide.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Plant Sciences
Yuka Maeyama, Yuta Nakashima, Hikaru Kato, Yuki Hitora, Kazuhiko Maki, Natsumi Inada, Shunya Murakami, Tomoaki Inazumi, Yuji Ise, Yukihiko Sugimoto, Hayato Ishikawa, Sachiko Tsukamoto
Summary: Amakusamine (1), a simple methylenedioxy dibromoindole alkaloid, was isolated from a marine sponge of the genus Psammocinia. It was found that compound 1 could inhibit the formation of multinuclear osteoclasts induced by RANKL, with an IC50 value of 10.5 µM. The structure-activity relationship of compound 1 was also investigated through synthetic derivatives.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Biochemistry & Molecular Biology
Ransong Ma, Yuanyuan Ren, Zhoubin Deng, Ke-Hu Wang, Junjiao Wang, Danfeng Huang, Yulai Hu, Xiaobo Lv
Summary: An efficient visible-light-induced radical cascade trifluoromethylation/cyclization reaction of inactivated alkenes with CF3Br has been developed in this work. The reaction produces valuable CF3-containing polycyclic aza-heterocycles including trifluoromethyl polycyclic quinazolinones, benzimidazoles, and indoles under mild reaction conditions. The method shows wide functional group compatibility and a broad substrate scope, providing a facile strategy for the pharmaceutical synthesis of these compounds.
Article
Chemistry, Organic
Matteo Faltracco, Said Ortega-Rosales, Elwin Janssen, Razvan C. Cioc, Christophe M. L. Vande Velde, Eelco Ruijter
Summary: The unexpected discovery in a seemingly trivial reaction led to the selective formation of a new carbazole product. This reaction, by carefully varying substituents, revealed a complex cascade mechanism with at least 10 elementary steps that could be directed towards different carbazole derivatives.
Article
Chemistry, Medicinal
Lu-Ting Dai, Li Yang, Fan-Dong Kong, Qing-Yun Ma, Qing-Yi Xie, Hao-Fu Dai, Zhi-Fang Yu, You-Xing Zhao
Summary: Four new indole-diterpenoids, along with twelve known ones, were isolated from the fermentation broth produced by adding L-tryptophan to the culture medium of the marine-derived fungus Penicillium sp. KFD28. Some of these compounds showed cytotoxicity against cancer cell lines and antibacterial activities against Staphylococcus aureus and Bacillus subtilis.
Article
Chemistry, Organic
Maurycy Prystupa, Tilo Sohnel, Jonathan Sperry
Summary: This study reports a method for synthesizing the putative bisindigotin structure by strategically ordering oxidative dimerization, reduction, and dehydration events, as well as a rearrangement method using p-TSA.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Medicinal
Weiwen Lin, Hanpeng Li, Zhiwen Wu, Jingyi Su, Zehong Zhang, Li Yang, Xianming Deng, Qingyan Xu
Summary: This article reports the discovery of new indole diterpenoids from the fungus Penicillium brefeldianum isolated from an abalone aquaculture base in Fujian province, China. Some of these compounds exhibited promising cytotoxic activities against cancer cell lines.
Review
Biochemistry & Molecular Biology
Masaru Enomoto
Summary: Indole diterpenoids are a large family of natural products with a hybrid molecular architecture of an indole nucleus and diterpenoid moiety, exhibiting important biological properties and intriguing molecular structures. The concise total synthesis of these compounds has been achieved through the development of efficient synthetic methods. In the past decade, several research groups have successfully completed total syntheses of various types of indole diterpenoids.
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY
(2021)
Article
Chemistry, Organic
Jiahang Yan, Yanxia Zhen, Pengyan Wang, Yimeng Han, Huanhuan Zou, Junhan Chen, Weigang He, Weiqing Xie
Summary: In this study, a de novo synthesis of the bisindole alkaloid geissolosimine was accomplished, along with the synthesis of related compounds and the demonstration of an innovative strategy. These findings provide new insights for further research.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Nicole Hauser, Michael A. Imhof, Sarah S. Eichenberger, Tomas Kundig, Erick M. Carreira
Summary: The first total syntheses of the indole diterpenoids (+)-shearinine G and D were achieved through late-stage coupling, diastereoselective intramolecular cyclopropanation, Sharpless dihydroxylation/Achmatowicz reaction, and Prins cyclization. Tuning of the substituents on the parent arylcarboxaldehyde led to divergent products, further transformed into shearinines G and D, with unexpected stereochemical outcomes in the Riley-type oxidation of a bicyclic enone.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Beiling Gao, Fengjie Yao, Zhaodong Zhang, Hanfeng Ding
Summary: A bioinspired photo-Fries/imine capture cascade reaction was developed in continuous-flow mode for the rapid construction of a series of diversely functionalized 2,7-heterocycle-fused tetrahydrocarbazoles, which are core structures in strychnos and akuammiline-type monoterpene indole alkaloids. The synthetic utility of this novel method has been demonstrated through the total synthesis of (+)-alsmaphorazine C and formal synthesis of (+)-strictamine in a concise and efficient manner.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Zhao Jinxiao, Wei Tonghui, Ke Sen, Li Yi
Summary: A one-step radical tandem cyclization reaction was developed for the synthesis of difluoroalkylindoles with quaternary carbon centers using difluorobromoesters as the fluorine source and 3-alkenyl indoles as the substrates under visible light-catalyzed conditions. The method is easy-to-operate and mild in conditions, with a wide range of substrate adaptability and good yields, providing a green and efficient synthetic route for fluorine-containing polycyclic indoles.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zheng Li, Zhiqiang Wang, Zeshuai Zhang
Summary: This method describes the switchable synthesis of 2-methylene-3-aminoindolines and 2-methyl-3-aminoindoles using a one-pot three-component reaction. It utilizes an inexpensive and easy-to-handle solid alkyne source as a replacement for flammable and explosive gaseous acetylene. The method offers a wide scope of substrates, satisfactory yield, and a simple workup procedure.
Article
Chemistry, Applied
Boonyanoot Chaiyosang, Kwanjai Kanokmedhakul, Natanong Yodsing, Sophon Boonlue, Jian-Xiong Yang, Yan Alexander Wang, Raymond J. Andersen, Jantana Yahuafai, Somdej Kanokmedhakul
Summary: Three new indole diterpenoids, aculeatupenes A-C (1-3), were isolated from the mycelium of Aspergillus aculeatus KKU-CT2, along with four known compounds. Compounds 1, 2, and emindole SB (4) exhibited weak cytotoxicity against various cancer cell lines, while compound 3 showed weak cytotoxicity against a specific cell line and no cytotoxicity against another. Compound 1 also showed weak antibacterial activity against Bacillus cereus.
NATURAL PRODUCT RESEARCH
(2022)
Article
Chemistry, Physical
Chunhui Liu, Ben Bradshaw, Feliu Maseras, Josep Bonjoch, Maria Besora
Article
Plant Sciences
Caroline Bosch, Ben Bradshaw, Josep Bonjoch
JOURNAL OF NATURAL PRODUCTS
(2019)
Article
Chemistry, Organic
Sergi Jansana, Faiza Diaba, Josep Bonjoch
Article
Chemistry, Multidisciplinary
Sergi Jansana, Guilhem Coussanes, Jordi Puig, Faiza Diaba, Josep Bonjoch
HELVETICA CHIMICA ACTA
(2019)
Article
Chemistry, Organic
Mar Saladrigas, Josep Bonjoch, Ben Bradshaw
Review
Chemistry, Organic
Josep Bonjoch, Faiza Diaba
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Mar Saladrigas, Jordi Puig, Josep Bonjoch, Ben Bradshaw
Article
Chemistry, Organic
Claudia Marques, Faiza Diaba, Enrique Gomez-Bengoa, Josep Bonjoch
Summary: A synthetic approach to functionalized ABC-tricyclic framework of calyciphilline A-type alkaloids is reported, which involves radical cyclization and stereocontrolled aldol cyclization. The resulting compound serves as a building block for this class of alkaloids, and the synthesis of azatricyclic compound I constitutes a formal synthesis of himalensine A.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Luis Bustos, Carlos Echiburu-Chau, Alejandro Castro-Alvarez, Ben Bradshaw, Mario J. Simirgiotis, Marco Mellado, Claudio Parra, Mauricio Cuellar
Summary: This study determined the cytotoxicity of eleven chalcones synthesized from two acetophenones and investigated their possible mechanisms. Two chalcones showed significant inhibitory effects and are potential candidates for further research and development.
Article
Chemistry, Organic
Laura G. Rodriguez, Ana Delgado, Carlos J. Ciudad, Veronique Noe, Josep Bonjoch, Ben Bradshaw
Summary: A two-step reaction was developed to synthesize a ring system found in natural products. The reaction was explored with eight substituted nitrobenzenes, achieving yields of up to 87%. One of the benzazocine compounds, 4h, exhibited high cytotoxicity and was active against eight cancer cell lines.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Maximiliano Martinez-Cifuentes, Emmanuel Soto-Tapia, Camila Linares-Pipon, Ben Bradshaw, Paulina Valenzuela-Hormazabal, David Ramirez, Patricio Munoz-Torres, Claudio Parra
Summary: This study proposes the design of beta-keto esters as antibacterial compounds. By synthesizing eight beta-keto ester analogues and conducting computational analysis, compound 8 was found to have the most promising potential. In vitro antimicrobial screening showed that compounds 6 and 8 exhibited the most promising activity against the panel of bacteria studied.
Article
Chemistry, Organic
Claudia Marques, Faiza Diaba, Jaume Roca, Josep Bonjoch
Summary: The 5-endo-trig radical cyclization of N-benzyl-N-[(2-substituted)cycloalkenyl] trichloroacetamides using Bu3SnH and AIBN provides access to 3a-methyl- and 3a-methoxycarbonyl enelactams. Diastereoselective enolate alkylation of these enelactams leads to the synthesis of a set of 3-substituted derivatives, which can be further reduced to generate polyfunctionalized cis-octahydroindoles containing three consecutive stereocenters at C-3, C-3a, and C-7a. These building blocks can also be synthesized through an initial reductive radical cyclization using (carbo-substituted)dichloroacetamides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(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)
