Article
Chemistry, Organic
Peng-Zhen Sheng, Lu-Lu Li, Zhi-Bin Ni, Kun Wei, Yu-Rong Yang
Summary: Cephalotine A, a newly isolated alkaloid from Cephalotaxus, was successfully synthesized enantioselectively via three crucial reactions. These involved SmI2-mediated radical cyclization of lactone and aldehyde for the final ring formation, Chang's iridium-catalyzed C-H amidation for constructing pyrrolidone stereoselectively, and Carreria's dual Ir/amine catalyzed allylation to introduce the neighboring tertiary stereocenters.
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
Didier F. Vargas, Teodoro S. Kaufman, Enrique L. Larghi
Summary: The first total synthesis of marine alkaloid aqabamycin G was disclosed, involving addition to maleimide of an indole motif and a substituted diazo-benzenoid unit derived from acetaminophen. An alternative strategy using a protected phenol was also reported.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Li-Xuan Li, Long Min, Tian-Bing Yao, Shu-Xiao Ji, Chuang Qiao, Pei-Lin Tian, Jianwei Sun, Chuang-Chuang Li
Summary: The first total synthesis of daphgraciline, a member of Daphniphyllum yuzurine-type alkaloids, has been achieved. The unique structure of the yuzurine-type subfamily was efficiently assembled using a novel method, and the complex skeleton and key moiety were successfully constructed. This study provides a foundation for the further synthesis of enantioenriched daphgraciline with high stereochemistry.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Jia-Tian Lu, Yingxiao Zong, Xiaodong Yue, Junke Wang
Summary: The enantioselective synthesis of (+)-isolysergol was achieved in 18 steps with an overall yield of 11% from (2R)-(+)-phenyloxirane. Key steps included a stereoselective intramolecular 1,3-dipolar addition of nitrone with terminal olefin and a Cope elimination to form the D ring. A rhodium-catalyzed intramolecular [3 + 2] annulation of a benzene ring with alpha-imino carbenoid was designed for the late-stage synthesis of the 3,4-fused indole scaffold.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jianquan Zhu, Chao Zhang, Luyi Liu, Chaoyun Xue, Yukun Cai, Xiao-Yu Liu, Fei Xue, Yong Qin
Summary: This paper presents an asymmetric total synthesis of the sarpagine alkaloid (-)-normacusine B. The key features of this synthesis include a photocatalytic nitrogen-centered radical cascade reaction, a titanium-mediated intramolecular amide-alkene coupling, and a nickel-catalyzed reductive Heck coupling.
Article
Chemistry, Organic
Hongbin Zhai, Zhenhua Wang, Kewei Chen, Tian-Yu Sun, Jian Wei, Yun-Dong Wu
Summary: The first asymmetric total synthesis of indole alkaloid arbophyllidine has been achieved, featuring key reactions such as intramolecular reductive Heck reaction, Fischer indolization, and oxidative lactonization. Density functional theory calculations were employed to provide a comprehensive understanding of the oxidative lactonization.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Si-Hua Hou, Adriana Y. Prichina, Guangbin Dong
Summary: The development of a deconstructive strategy for the first asymmetric synthesis of (-)-thebainone A was described, utilizing an enantioselective C-C bond activation and a C-O bond cleavage reaction. The newly optimized conditions show broad substrate scope and excellent enantioselectivity (up to 99.5:0.5 er). The synthesis of (-)-thebainone A was completed by taking advantage of boron-mediated ether bond cleavage through two complementary routes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Multidisciplinary Sciences
Yingfu Lin, Rui Zhang, Di Wang, Tim Cernak
Summary: Efficient chemical synthesis is crucial for meeting the future demands of pharmaceuticals, materials, and agrochemicals. While the automation of retrosynthetic analysis for moderately complex molecules has been ongoing for decades, the vast number of possible routes has posed challenges for computer hardware and software until recently. In this study, we introduce a computational strategy that combines computer-aided synthesis planning with molecular graph editing to minimize the synthetic steps needed for producing alkaloids. Through the utilization of high-impact key steps identified in computer-generated retrosynthesis plans using graph edit distances, we have successfully achieved an enantioselective three-step synthesis of (-)-stemoamide.
Article
Chemistry, Multidisciplinary
Niklas Rauscher, Line Noesborg, Christian Jandl, Thorsten Bach
Summary: In this study, the prezizane-type sesquiterpene agarozizanol B was synthesized through a photochemical cascade reaction, successfully achieving the key step of the synthesis with a specific strategy and obtaining the (+)-enantiomer that is identical to the natural product.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Brendan Horst, Daniel S. Verdoorn, Sven Hennig, Gydo van der Heijden, Eelco Ruijter
Summary: We report a novel method for the synthesis of monoterpene indole alkaloids through an intramolecular conjugate addition/Truce-Smiles/Elcb cascade reaction. This method was successfully applied to the asymmetric total synthesis of several natural products, demonstrating its potential for the synthesis of other compounds as well.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Liu-Yang Pu, Fan Yang, Ji-Qiang Chen, Ying Xiong, Jian-Hua Xie, Qi-Lin Zhou
Summary: The enantioselective total synthesis of the pentacyclic proaporphine alkaloid (-)-misramine was achieved, featuring key reactions including Pictet-Spengler cyclization and Baeyer-Villiger oxidation. The absolute configuration of the pentacyclic framework was determined through X-ray single-crystal analyses.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Kuei-Wei Chiu, Yu-Hsun Tseng, Ying-Xin Li, Rong-Jie Chein
Summary: In this study, a novel biomimetic synthesis of clavicipitic acid diastereomers was reported, utilizing a DDQ-mediated crossdehydrogenative coupling (CDC) reaction. The synthesis involved Suzuki coupling for prenylation and an intramolecular CDC reaction for the construction of the azepinoindole core. The trans isomer was obtained as the major product, and the two diastereomers were separable. The CDC reaction conditions were investigated, and a plausible mechanism for diastereoselectivity was proposed.
Article
Chemistry, Organic
Qingsong Deng, Aimin Yu, Shunguang Zhang, Xiangtai Meng
Summary: A novel tunable domino reaction promoted by K2CO3 was developed for the synthesis of benzothiophene fused pyranone and thiochromen fused furan derivatives by adjusting MgSO4. The reaction involves C-S bond cleavage induced by K2CO3 followed by two-step condensation reactions. The significance of these novel domino reactions lies in the production of products that are not easily accessible via traditional synthetic methods.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Andrew G. Dalling, Georg Spath, Alois Furstner
Summary: This article reports the first total synthesis of a tetracyclic marine pyridinium alkaloid, which was achieved using recent advances in chemoselectivity management. The synthesis involved the formation of critical C-C bond using nickel/iridium photoredox dual catalysis, successful ring closing alkyne metathesis (RCAM) despite the presence of a Lewis acidic alkylidyne catalyst, and a unique iridium catalyzed hydrosilylation reaction. The synthesis also demonstrated site- and chemoselective intramolecular N-alkylation for closing the second strained macrocycle.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
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
Leonardus H. Leijendekker, Jens Weweler, Tobias M. Leuther, Daniel Kratz, Jan Streuff
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Inorganic & Nuclear
Philippe Weis, Clarissa Hettich, Daniel Kratzert, Ingo Krossing
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Daniel Kratzert, Ingo Krossing
JOURNAL OF APPLIED CRYSTALLOGRAPHY
(2019)
Article
Chemistry, Inorganic & Nuclear
Alexander N. Paesch, Anne-Kathrin Kreyenschmidt, Regine Herbst-Irmer, Dietmar Stalke
INORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Kim Glootz, Daniel Himmel, Daniel Kratzert, Burkhard Butschke, Harald Scherer, Ingo Krossing
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Editorial Material
Crystallography
Lennard Krause, Benedikt Niepoetter, Christian J. Schuermann, Dietmar Stalke, Regine Herbst-Irmer
CRYSTALLOGRAPHY REVIEWS
(2020)
Article
Chemistry, Multidisciplinary
W. Unkrig, M. Schmitt, D. Kratzert, D. Himmel, I. Krossing
Article
Chemistry, Physical
George C. Fish, Juan Manuel Moreno-Naranjo, Andreas Billion, Daniel Kratzert, Erwin Hack, Ingo Krossing, Frank Nuesch, Jacques-E Moser
Summary: The study demonstrates that a decrease in H-aggregation in organic salt semiconductors leads to reduced charge transfer, however, carrier mobility remains largely unchanged as a decrease in energetic disorder helps alleviate trapping of charges by H-aggregates.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2021)
Article
Chemistry, Multidisciplinary
Lukas D. Ernst, Konstantin Koessler, Andreas Peter, Daniel Kratzert, Harald Scherer, Burkhard Butschke
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Organic
Jan S. Woessner, David C. Grenz, Daniel Kratzert, Birgit Esser
ORGANIC CHEMISTRY FRONTIERS
(2019)
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)
Article
Chemistry, Multidisciplinary
Jan Schroeder, Daniel Himmel, Daniel Kratzert, Valentin Radtke, Sabine Richert, Stefan Weber, Tobias Boettcher
CHEMICAL COMMUNICATIONS
(2019)