Article
Chemistry, Organic
Arka Das, Christine Jonathan, Rana Saha, Md Imran Ahmed, Subhendu Bhowmik
Summary: A regioselective decarboxylative alkynylation of tetrahydro-beta-carboline-1-carboxylic acid under peroxide-free condition is reported, which exhibits high selectivity for the 1-position of tetrahydro-beta-carboline. Depending on the reagent, the reaction can produce alkynylated or enaminone products. The reaction proceeds through sequential decarboxylative iminium ion formation followed by an alkynylation and oxidative rearrangement cascade.
Article
Oncology
Xiaoyan Xing, Fahui Li, Yajie Hu, Lin Zhang, Qian Hui, Hongyu Qin, Qixiao Jiang, Wenyan Jiang, Chunyan Fang, Lei Zhang
Summary: This study identified potent APN inhibitors that could be used as lead compounds for tumor chemo-sensitization and cancer stem cell-based therapies.
FRONTIERS IN ONCOLOGY
(2022)
Article
Chemistry, Organic
Harshal D. Patel, Sebastian Gaggl, Lukas F. Pasteka, Thomas Fallon
Summary: The fluxional structure of bullvalene is expanded by the discovery of a [5,5]-sigmatropic rearrangement of dialkenyl substituted derivatives, leading to the formation of tetrahydro-1,8-ethenoheptalenes (THEH). The substitution pattern variation alters the product distribution, with one product thermodynamically balanced between THEH and bullvalene isomers.
Article
Chemistry, Applied
Da-Ping Jin, Shi-Qi Cao, Fu Cheng, Ze-Sen Xue, Run-Ze Li, Yan-Lin Pu, Dao-Yong Zhu, Wen Bao, Xue-Tao Xu, Shao-Hua Wang
Summary: An Au(I)-catalyzed cascade reaction involving cyclization and semipinacol rearrangement of 1,6-enynes has been developed for the synthesis of spiro[4.5]decanes and 7-azaspiro[4.5]decanes. The use of JohnPhosAuCl/NaBARF catalyst led to the formation of functionalizable spirocyclic products with high diastereoselectivity ranging from 6.7:1 to > 20:1 dr. A plausible reaction mechanism has been proposed based on previous literature and experimental findings.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Julian Baars, Isabelle Grimm, Dirk Blunk, Joerg-Martin Neudoerfl, Hans-Guenther Schmalz
Summary: A 12-step total synthesis of the natural product dysiherbol A was achieved, revealing the need for revision of the originally proposed structure and absolute configuration. The synthesis involved key steps including Cu-catalyzed addition/enolate-trapping, Au-catalyzed double cyclization, and late installation of the C5-bridgehead methyl group. Spectroscopic measurements confirmed the identity of the synthetic compound with the natural product but with an opposite molecular rotation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Medicinal
Rongguo Ren, Xiaofang Wang, Derek A. Leas, Cecile Haberli, Monica Cal, Yuxiang Dong, Marcel Kaiser, Jennifer Keiser, Jonathan L. Vennerstrom
Summary: Tetrahydro-gamma-carboline sulfonamides were discovered as a new type of antischistosomal drugs. Both aryl sulfonamide and tetrahydro-gamma-carboline substructures were essential for high antischistosomal activity. Increased polarity improved solubility and metabolic stability, but decreased antischistosomal activity. Two compounds with IC50 values < 5 mu M against ex vivo Schistosoma mansoni were identified.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Physical
Zhenguo Zhang, Xiaoxiao Liu, Liang Ji, Ting Zhang, Zhenhua Jia, Teck-Peng Loh
Summary: This study reveals the synthesis of diverse tetrahydro-beta-carbolines and spirocyclic tetrahydro-beta-carbolines through the unprecedented triarylcarbonium ion-pair-catalyzed reaction in water under metal-free conditions. The reaction shows good yields and excellent functional group tolerance, allowing for late-stage modification of natural products and small molecular drugs.
Article
Chemistry, Multidisciplinary
Rina Mahato, Chinmoy Kumar Hazra
Summary: In this study, pentafluorophenol was revealed as an effective catalyst for the synthesis of (spirocyclic) tetrahydro-beta-carbolines via the Pictet-Spengler reaction. This straightforward catalytic system operates under mild conditions, yielding indole alkaloids in excellent yield and exhibiting remarkable functional group tolerance, including late-stage modifications. This transformation provides a practical and adaptable approach for the gram-scale synthesis of the natural alkaloid Komavine and enables the synthesis of the commercial drug Tadalafil.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Jinmei Zhu, Lu Yang, Jiequn Wu, Zixin Deng, Xudong Qu
Summary: By improving the specificity synthesis method for sterically hindered amines, researchers successfully synthesized the important 1-aryl-tetrahydro-beta-carboline framework, providing a new approach for its application in natural products and pharmaceuticals.
Article
Chemistry, Multidisciplinary
Jun-Jie Yin, Yun-Peng Wang, Jun Xue, Feng-Fan Zhou, Xing-Qian Shan, Rong Zhu, Kun Fang, Lei Shi, Shu-Yu Zhang, Si-Hua Hou, Wujiong Xia, Yong-Qiang Tu
Summary: The first total syntheses of polycyclic diterpenes phomopsene (1), methyl phomopsenonate (2), and iso-phomopsene (3) have been achieved through an unusual cascade reorganization of C-C single bonds. This approach involves a synergistic Nazarov cyclization/double ring expansion for rapid and stereospecific construction of the tetraquinane scaffold, as well as a one-pot strategic ring expansion through Beckmann fragmentation/recombination to efficiently assemble the tetracyclic skeleton. The correct structure of iso-phomopsene was determined to be the C7 epimer of the originally assigned structure, and the absolute configurations of the target molecules were confirmed through enantioselective synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Aleksa Milosavljevic, Connor Holt, Alison J. Frontier
Summary: Herein, a one-pot nitrogen-interrupted halo-Prins/halo-Nazarov coupling cascade is reported, which enables the synthesis of functionalized cyclopenta[b]indolines with up to four contiguous stereocenters by joining an enyne and a carbonyl partner. A general method for alkynyl halo-Prins reaction of ketones is provided for the first time, allowing the formation of quaternary stereocenters. The outcomes of secondary alcohol enyne couplings and the impact of aniline enyne substituents on the reaction are also described.
Article
Chemistry, Inorganic & Nuclear
Xiuru Bi, Luyao Tao, Nan Yao, Mingxia Gou, Gexin Chen, Xu Meng, Peiqing Zhao
Summary: In this study, a H3PO4 center dot 12WO(3)/OMS-2 nanocomposite catalyst was successfully prepared, leading to the synthesis of β-carbolines and 3,4-dihydro-β-carbolines by tuning reaction conditions. The catalyst exhibited excellent activity, high selectivity, and good stability, providing a practical pathway for flexible and controllable synthesis of novel compounds.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Organic
Yiwen Zhu, Binghu Guo, Shenkui Gao, Jun Ying, Xiao-Feng Wu
Summary: A new cobalt-catalyzed carbonylative synthesis of free (NH)-tetrahydro-beta-carbolinones from tryptamine derivatives has been developed using a traceless directing group strategy. The reaction produced a variety of free (NH)-tetrahydro-beta-carbolinones in good yields. Moreover, late-stage modifications of several bioactive molecules could also be achieved.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Shubham Lata, Sourav Taru Saha, Mandeep Kaur, Paul Awolade, Oluwakemi Ebenezer, Parvesh Singh, Vipan Kumar, Vipan Kumar
Summary: This study designed and synthesized a series of tetrahydro-beta-carboline-naphthalimide hybrids. Through evaluating their growth inhibitory potential against breast cancer cell lines and studying their interactions with estrogen receptor, the success rate and potential of hybridization technique in cancer treatment were demonstrated.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Biochemistry & Molecular Biology
Vipin Kumar, Anjali Saxena, Ranjan Patra, Devalina Ray, Hong-yu Li, Biswajit Saha
Summary: Ugi-four component reaction (Ugi-4CR) is an attractive method for diversity-oriented and step economical synthesis, as shown by its past applications. In this study, we report a method for the synthesis of fused polycyclic beta-carboline derivatives through sequential Pictet-Spengler's and Ugi-4CR multi-component reactions followed by cascade cyclization. The resulting conformationally stable heterocyclic molecules are expected to have potential interactions with different biological targets. This methodology provides a simple and facile access to heterocycles embedded in polycyclic frameworks that are difficult to synthesize using conventional methods.
MOLECULAR DIVERSITY
(2023)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
