Article
Chemistry, Organic
Zhiyu Gao, Li Ren, Ruizhi Wang, Liang Shi, Yanhai Wang, Feng Su, Hong-Dong Hao
Summary: An intramolecular formal [3 + 2] cationic cycloaddition was used to synthesize codonopiloneolignanin A, and benzocycloheptene was identified as a good substrate for 1,3-dipolar cycloaddition. A model study was conducted to explore the synthesis of cephalocyclidine A skeleton.
Article
Chemistry, Organic
Jongyeol Han, Hosam Choi, Joohee Choi, Kiyoun Lee
Summary: The first total synthesis of tetrahydrofuran dilignangymnothelignan K is achieved by implementing an early stage one-carbon homologative lactonization for constructing the necessary scaffold and stereo-centers, along with acid-promoted dimerization and Suzuki-Miyaura cross-coupling reaction to install the challenging diaryl skeleton.
Article
Chemistry, Multidisciplinary
Di Zhang, Youyuan Xiong, Yingjie Guo, Lei Zhang, Zheng Wang, Kuiling Ding
Summary: In this study, a Pd-catalyzed enantioselective domino Heck carbonylation reaction was developed using o-iodoacrylanilides, terminal alkynes, and water as nucleophiles. The reaction afforded a diverse range of beta-carbonylated 2-oxindole derivatives with a 3,3-disubstituted all-carbon quaternary stereocenter in high yields and good to excellent enantioselectivities. The synthetic utility of the methodology was demonstrated through gram-scale synthesis of various compounds, showcasing its potential for efficient chiral 2-oxindole synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Andrew Whyte, Jonathan Bajohr, Ramon Arora, Alexa Torelli, Mark Lautens
Summary: An enantioselective consecutive cyclization/coupling process catalyzed by palladium was reported in this study. The stereoinduction was achieved through an enantioselective carbopalladation, leading to the generation of an intermediate that promotes a nucleopalladation step. This dual cyclization sequence was compatible with various nucleophiles and aryl iodides, producing numerous bisheterocycles in good yields and high regio- and enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Biochemistry & Molecular Biology
Liangxin Fan, Xinxin Zhu, Xingyuan Liu, Fangyu He, Guoyu Yang, Cuilian Xu, Xifa Yang
Summary: This review summarizes recent developments in the synthesis of these tricyclic indoles with palladium-catalyzed domino reactions and their applications in the total synthesis of representative natural products.
Article
Chemistry, Multidisciplinary
Zorana Ferjancic, Andrej Kukuruzar, Filip Bihelovic
Summary: An enantioselective total synthesis of the monoterpenoid indole alkaloid (+)-alstonlarsine A (1) has been achieved, which possesses a unique pentacyclic skeleton and rare biological activity. The key step involves an efficient domino sequence, consisting of enamine formation followed by an inverse-electron-demand intramolecular dearomative Diels-Alder cycloaddition for the construction of a 9-azatricyclo[4.3.1.0(3,8)]decane core. This strategy offers a new general entry into other tricyclic frameworks with fused indole ring and 6-, 7-, or 8-membered rings.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Zorana B. Ferjancic, Filip J. Bihelovic
Summary: This article focuses on the total synthesis of (+)-Alstonlarsine A and a novel methodology for indole C2 functionalization, providing new insights for the synthesis of other indole alkaloids.
Article
Chemistry, Organic
Shingo Takiguchi, Yuki Hirota-Takahata, Takahide Nishi
Summary: The absolute configuration of ogipeptins has been elucidated by the successful total synthesis of ogipeptin A.
Article
Chemistry, Applied
Antonio Arcadi, Giancarlo Fabrizi, Antonella Goggiamani, Antonia Iazzetti, Federica Iavarone, Federico Marrone, Giulia Mazzoccanti, Alessio Sferrazza
Summary: A palladium-catalyzed domino approach has been developed for the synthesis of challenging phenanthrene derivatives. The procedure involves a sequence of oxidative homocoupling, cyclization, and oxidation starting from deoxybenzoin derivatives ortho-halogenated. Good assembly efficiency and functional group tolerance were observed with yields ranging from moderate to excellent. A plausible reaction mechanism has been proposed based on experimental results and literature data.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Shivani Gayyur, Shivani Choudhary, Ruchir Kant, Nayan Ghosh
Summary: A straightforward and atom-economical one-pot protocol catalyzed by gold(I) and zinc(II) has been demonstrated for the synthesis of amine-substituted diaryl[c,h][1,6]naphthyridines from two different aromatic nitriles. This dual-catalytic strategy is highly efficient and yields a variety of tetracyclic heteroaromatic products in good to excellent yields. Furthermore, the base can efficiently catalyze the second annulation step, resulting in structurally unique thiophene-fused [1,6]naphthyridines with good yields.
Article
Chemistry, Multidisciplinary
Mengmeng Xu, Min Hou, Haibing He, Shuanhu Gao
Summary: This study developed a new synthetic method for constructing aryltetralin lactone lignans and successfully synthesized several natural lignans using this methodology. The synthesized aglacins and small-molecule library created new opportunities for SAR studies of the podophyllotoxin family of natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Xavier Abel-Snape, Gina Wycich, Mark Lautens
Summary: A palladium-catalyzed three-component domino reaction for accessing indene derivatives is described. The reaction involves the sequential formation of three bonds, with the first two resulting from inter- and intramolecular carbopalladation, and the final bond arising from an attack by a terminating nucleophilic reagent. The starting tether on the iodoarene can be modified to yield either indenes or benzofulvenes. Additionally, the use of an oxabicycle as an acetylene surrogate is demonstrated, and the enantioselective synthesis of indenes is preliminarily explored.
Review
Chemistry, Organic
Han-Qiu Zhang, Chu-Xuan Yan, Jian Xiao, Ya-Wen Wang, Yu Peng
Summary: This review discusses the synthetic progress of bioactive 2,7'-cyclolignans, focusing on the chemical synthesis methods like Pd-catalyzed C-H arylation and organocatalysis. The newly developed methods aim to stimulate further development of novel synthetic strategies for natural products with important biological activities.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Shinya Shiomi, Kaewsri Wilailak, Wataru Soutome, Hiromitsu Takayama, Mariko Kitajima, Hayato Ishikawa
Summary: A first asymmetric total synthesis of huperzine H has been achieved in a 12% overall yield from commercially available (+)-pulegone. The relative and absolute stereochemistry of huperzine H is established through key reactions including a highly diastereoselective Mukaiyama-Michael addition reaction and an intramolecular S(N)2 cyclization reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Feng-Yuan Wang, Lei Jiao
Summary: An asymmetric total synthesis of cage-like indole alkaloid arborisidine is achieved using a new synthetic strategy that involves a catalytic parallel kinetic resolution based on ambident nucleophilicity of indole and a 5-exo-trig radical cyclization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Anna Hanft, Malte Juergensen, Ruediger Bertermann, Crispin Lichtenberg
Article
Chemistry, Multidisciplinary
Kresimir Molcanov, Zhongyu Mou, Miklos Kertesz, Biserka Kojic-Prodic, Dietmar Stalke, Serhiy Demeshko, Ana Santic, Vladimir Stilinovic
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Wenling Li, Christian Koehler, Zhi Yang, Dietmar Stalke, Regine Herbst-Irmer, Herbert W. Roesky
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Multidisciplinary
Mujahuddin M. Siddiqui, Samir Kumar Sarkar, Soumen Sinhababu, Paul Niklas Ruth, Regine Herbst-Irmer, Dietmar Stalke, Munmun Ghosh, Mingxing Fu, Lili Zhao, David Casanova, Gernoty Frenking, Brigitte Schwederski, Wolfgang Kaim, Herbert W. Roesky
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Inorganic & Nuclear
Alexander N. Paesch, Anne-Kathrin Kreyenschmidt, Regine Herbst-Irmer, Dietmar Stalke
INORGANIC CHEMISTRY
(2019)
Article
Chemistry, Inorganic & Nuclear
Wenling Li, Subrata Kundu, Christian Koehler, Jiancheng Li, Sayan Dutta, Zhi Yang, Dietmar Stalke, Regine Herbst-Irmer, A. Claudia Stueckl, Brigitte Schwederski, Debasis Koley, Wolfgang Kaim, Herbert W. Roesky
Article
Chemistry, Multidisciplinary
Christian Koehler, Jens Luebben, Lennard Krause, Christina Hoffmann, Regine Herbst-Irmer, Dietmar Stalke
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS
(2019)
Article
Chemistry, Multidisciplinary
Soumen Sinhababu, Mujahuddin M. Siddiqui, Samir Kumar Sarkar, Annika Muench, Regine Herbst-Irmer, Anjana George, Pattiyil Parameswaran, Dietmar Stalke, Herbert W. Roesky
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Review
Chemistry, Inorganic & Nuclear
Johannes Kretsch, Ingo Koehne, Mart Lokov, Ivo Leito, Dietmar Stalke
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Filippo M. Perna, Aurelia Falcicchio, Antonio Salomone, Anne Milet, Rosanna Rizzi, Ghanem Hamdoun, Gabriella Barozzino-Consiglio, Dietmar Stalke, Hassan Oulyadi, Vito Capriati
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Inorganic & Nuclear
Mingdong Zhong, Yashuai Liu, Subrata Kundu, Nico Graw, Jiancheng Li, Zhi Yang, Regine Herbst-Irmer, Dietmar Stalke, Herbert W. Roesky
INORGANIC CHEMISTRY
(2019)
Editorial Material
Crystallography
Lennard Krause, Benedikt Niepoetter, Christian J. Schuermann, Dietmar Stalke, Regine Herbst-Irmer
CRYSTALLOGRAPHY REVIEWS
(2020)
Article
Chemistry, Inorganic & Nuclear
Samir Kumar Sarkar, Mujahuddin M. Siddiqui, Subrata Kundu, Munmun Ghosh, Johannes Kretsch, Peter Stollberg, Regine Herbst-Irmer, Dietmar Stalke, A. Claudia Stueckl, Brigitte Schwederski, Wolfgang Kaim, Sagar Ghorai, Eluvathingal D. Jemmis, Herbert W. Roesky
DALTON TRANSACTIONS
(2019)
Article
Chemistry, Multidisciplinary
Soumen Sinhababu, Subrata Kundu, Mujahuddin M. Siddiqui, Alexander N. Paesch, Regine Herbst-Irmer, Brigitte Schwederski, Pinaki Saha, Lili Zhao, Gernot Frenking, Wolfgang Kaim, Dietmar Stalke, Herbert W. Roesky
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Jiancheng Li, Mingdong Zhong, Helena Keil, Hongping Zhu, Regine Herbst-Irmer, Dietmar Stalke, Sriman De, Debasis Koley, Herbert W. Roesky
CHEMICAL COMMUNICATIONS
(2019)
