Article
Chemistry, Multidisciplinary
Lixin Liang, Shiqiang Zhou, Wei Zhang, Rongbiao Tong
Summary: Two complementary approaches were developed for the catalytic asymmetric alkynylation of 3,4-dihydro-beta-carbolinium ions with up to 96 % yield and 99 % ee. The utility of chiral C1-alkynyl TH beta Cs was demonstrated through the total synthesis of seven indole alkaloids.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Yulong Zhao, Jiaxin Li, Ruize Ma, Feifei He, Hongliang Shi, Xiaoguang Duan, Huilin Li, Xingang Xie, Xuegong She
Summary: The total synthesis of the indole alkaloid (-)-an-dranginine has been achieved in 10 steps, involving key reactions including nucleophilic addition of acetylenyl anion, intramolecular N-alkylation reaction, and dienyne metathesis cascade reaction.
Article
Chemistry, Organic
Shiyuan Kang, Yinxia Wu, Min Hu, Ying Ma, Xiangdi Huang, Zhen Hao, Xiujuan Li, Wen Chen, Hongbin Zhang
Summary: The asymmetric total synthesis of vinorine, a complex cage-like alkaloid, has been achieved using a flexible approach. Key steps in this synthesis involve a rearrangement/cyclization reaction to form the functional 9-azabicyclo[3.3.1]nonane scaffold, a high yield indole annulation to create a common intermediate for sarpagine-ajamaline type alkaloids, and a rearrangement reaction to construct the C15-C20 bond.
Article
Chemistry, Organic
Niklavs Udris, Kristaps Jaudzems, Gints Smits
Summary: The stereoselective total synthesis of a proposed potent serotonin 5-HT1A receptor agonist uncarialin A was achieved with a 17% overall yield using meroquinene tert-butyl ester as the chiral synthon. Spectral differences between the synthetic product and the sample isolated from natural sources suggest a need to revise the structure of the natural product.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Eunjoon Park, Cheolwoo Bae, Cheon-Gyu Cho, Cheol-Hong Cheon
Summary: The total syntheses of the antirhine alkaloids were achieved through a series of reactions, including the cyanide-catalyzed imino-Stetter reaction and subsequent C-ring formation to generate the key intermediate. The trans-selective installation of the homoallylic alcohol side-chain at C-15 allowed the successful total syntheses of antirhine and its known epimer.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Remi Andres, Qian Wang, Jieping Zhu
Summary: A divergent asymmetric total synthesis of voacafricines A and B, hexacyclic monoterpene indole alkaloids, has been achieved by several key steps, including a catalyst-controlled asymmetric Pictet-Spengler reaction, oxidative cleavage, and intramolecular nucleophilic addition. The synthesis confirmed the absolute configuration of these natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
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, Multidisciplinary
Guang Li, Nicolas Gaeng, Cyril Piemontesi, Qian Wang, Jieping Zhu
Summary: The enantioselective total synthesis of three monoterpene indole alkaloids was successfully achieved by introducing chirality, using MOM ether as a protective group, and employing a domino reaction to construct the indole and piperidine rings. The synthesis confirmed the absolute configuration of these natural products according to the biogenetic hypothesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(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
Yi An, Mengjuan Wu, Weijian Li, Yaling Li, Zhenzhen Wang, Yansong Xue, Pei Tang, Fener Chen
Summary: The work reported a concise and enantioselective total synthesis of the Schizozygine alkaloid (-)-strempeliopine. A synthetic strategy featuring palladium-catalyzed decarboxylative asymmetric allylic alkylation and diastereoselective Bischler-Napieralski/lactamization was developed to construct the pentacyclic core structure with complete control of four neighbouring stereocenters.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Kosuke Okada, Ken-ichi Ojima, Hirofumi Ueda, Hidetoshi Tokuyama
Summary: The synthesis of (+)-pleiocarpamine, (+)-voacalgine A and (+)-bipleiophylline was achieved in this study. The 10-step synthesis of (+)-pleiocarpamine features the construction of stereochemistry at the C16 position by radical cyclization and the synthesis of the highly strained cage-like structure via Pd-catalyzed intramolecular aromatic C-H functionalization. By modifying the biomimetic aerobic oxidative coupling of tryptophane derivatives catalyzed by FePc(CO2H)(8), the oxidative coupling of (+)-pleiocarpamine with pyrocatechuic acid produced (+)-voacalgine A. The total synthesis of (+)-bipleiophylline was completed by the second coupling of (+)-voacalgine A with (+)-pleiocarpamine or the one-pot couplings of 2 equiv of (+)-pleiocarpamine with pyrocatechuic acid.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
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, Applied
Rongxing Zhang, Zhijie Wu, Shaoqian Yang, Dawei Ma
Summary: An asymmetric approach to install substituted imidazo[1,2-a]-indol-3-ones was reported in this study, which relied on a Pd/diamidophosphite-catalyzed intramolecular dearomative allylic substitution of 1,3-disubstituted indoles derived from 3-formylindoles and amino acids. Enantioselective total syntheses of (-)-spiroquinazoline and three related alkaloids were successfully achieved.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Organic
Athira Parammal, Manoj Kumar, Shubham Singh, Joe Sam Xavier, Parthasarathi Subramanian
Summary: This review discusses the synthetic strategies and total synthesis methods of aspidofractinine and its analogues. Aspidofractinine is a natural product with fascinating structural features and biological activities, making its synthesis highly significant.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
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
Timea Szabo, Marcell Papp, Dora Rita Nemeth, Andras Dancso, Balazs Volk, Matyas Milen
Summary: The synthesis of variously substituted indolo[2,3-c]quinolin-6(7H)-ones via Pd-catalyzed intramolecular C-H arylation provides a new approach for the synthesis of antimalarial isoneocryptolepine analogues. Quantum chemical calculations suggest a plausible trigonal bipyramidal concerted metalation-deprotonation transition state in the ring closure mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Imre Gyujto, Marta Porcs-Makkay, Gergo Szabo, Zsolt Kelemen, Gyongyver Pusztai, Gabor Toth, Andras Dancso, Judit Halasz, Gyula Simig, Balazs Volk, Laszlo Nyulaszi
Summary: The base-induced rearrangement reactions of 3,4-dihydro-2H-1,2,3-benzothiadiazine 1,1-dioxides result in the formation of new C-N bonds with the position of the bond dependent on the amount of base used. DFT calculations and detailed NMR studies clarified the mechanism of the reaction, including the formation of mono- or dianionic key intermediates. The role of an enamide intermediate formed during the reaction process was also investigated.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Gabor Gyorke, Andras Dancso, Balazs Volk, Matyas Milen
Summary: Copper catalysis plays a crucial role in synthetic organic chemistry, but the catalytic activity of copper-containing minerals has been underrepresented in literature. This study highlights the potential use of readily available ores like bornite and chalcocite for catalyzing organic reactions, with promising results in terms of yield and reusability. By utilizing these minerals, high-polluting industrial copper production can be avoided, making the process more economical and environmentally friendly.
Review
Biochemistry & Molecular Biology
Timea Szabo, Balazs Volk, Matyas Milen
Summary: Beta-carboline alkaloids are a diverse family of compounds with various biological activities, making them desirable drug candidates. Researchers have made significant progress in the synthesis of these alkaloids in recent years.
Article
Chemistry, Organic
Gyorgyi Kovanyi-Lax, Csilla Hargitai, Peter Abranyi-Balogh, Tamas Nagy, Gabor Toth, Zsofia Garadi, Gabor Nemeth, Angela Pandur, Simon Horvath, Andras Dancso, Gyula Simig, Balazs Volk
Summary: In this study, the reactions of ortho-(pivaloylaminomethyl)benzaldehydes using boron trifluoride diethyl etherate (BF3 center dot OEt2) as the catalyst were described, and the formation of a new dimer-like keto compound and an oxoindene-type by-product was observed. Detailed characterization and theoretical calculations support the proposed mechanisms and explain the product distribution.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Physical
Gabor Gyorke, Andras Dancso, Balazs Volk, Laszlo Bezur, David Hunyadi, Imre Szaloki, Matyas Milen
Summary: Copper-containing minerals play a vital role in the economy and the origin of life. This study presents a copper mineral-catalyzed method for synthesizing arylated amide derivatives, utilizing the catalytic effect of readily available minerals.
Article
Pharmacology & Pharmacy
Bence Sipos, Ildiko Csoka, Nimrod Szivacski, Maria Budai-Szucs, Zsuzsanna Schelcz, Istvan Zupko, Piroska Szabo-Revesz, Balazs Volk, Gabor Katona
Summary: Intranasally administered NSAIDs can be effective in pain management, and nanoemulsions can enhance drug absorption and bioavailability, providing an advanced drug delivery system.
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES
(2022)
Article
Chemistry, Applied
Balint Petho, Gabor B. Szilagyi, Bela Mengyel, Tamas Nagy, Ferenc Farkas, Katalin Katai-Fadgyas, Balazs Volk
Summary: A flow chemical approach was developed to mitigate the hazards associated with aromatic nitration and catalytic hydrogenation. A four-step uninterrupted process, based on a newly developed heterogeneous flow reactor system and a custom-made liquid-liquid extractor, was successfully used for the efficient production of a key intermediate of the drug candidate afizagabar (S44819).
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Organic
Balint Nyulasi, Tamara Teski, Andras Gy. Nemeth, Sara Sprober, Gyula Simig, Balazs Volk
Summary: The significant pharmacological activity of 2,3-benzodiazepine-4-ones has increased interest in this compound family. However, there is limited literature on the closely related 2,3,4-benzothiadiazepine 2,2-dioxides. In this study, a new synthetic route was explored using highly versatile intermediates to expand the reaction to a wider range of aromatic substitutions and to prepare 5-alkyl and 5-H derivatives.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Attila M. Remete, Melinda Nonn, Balazs Volk, Lorand Kiss
Summary: Due to the relevance of fluorine-containing organic molecules in drug research, the synthesis of organofluorine scaffolds is highly significant in synthetic organic chemistry. Trifluoromethylative difunctionalizations of carbon-carbon multiple bonds, with the introduction of a CF3 group and another function, have great potential. Alkynyltrifluoromethylation reactions, especially, are gaining interest in synthetic chemistry. This review summarizes recent developments in alkynyltrifluoromethylation reactions, including reactions involving intramolecular alkynyl migration and intermolecular transformation, as well as reactions of alkynes.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Timea Szabo, Funda Lidya Gorur, Simon Horvath, Balazs Volk, Matyas Milen
Summary: A new synthetic approach for the total synthesis of the pharmacologically active beta-carboline alkaloid brevicolline is described. The method allows for the practical synthesis of the racemic target molecule, the natural (S)-enantiomer, and its antipode. The synthetic route has been developed to improve the overall yield compared to previously reported methods.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Matyas Milen, Balint Nyulasi, Tamas Nagy, Gyula Simig, Balazs Volk
Summary: A novel synthesis approach for the late-stage tetracyclic key intermediate of lumateperone starting from commercially available quinoxaline is described. The tetracyclic skeleton was constructed efficiently using Fischer indole synthesis, with the advantage of inexpensive starting material and avoidance of borane-based reduction step, providing potential for scalability.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
