Article
Chemistry, Organic
David L. Cain, Niall A. Anderson, David B. Cordes, Alexandra M. Z. Slawin, Allan J. B. Watson
Summary: A concise strategy for the total synthesis of several Aspidosperma alkaloids has been reported. The strategy involves a Suzuki-Miyaura cross-coupling and a Diels-Alder cascade reaction, leading to the synthesis of a common intermediate for Aspidosperma alkaloids. This intermediate has been successfully utilized for the synthesis of four different natural products.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Atsushi Nakayama, Tenta Nakamura, Toshihiro Zaima, Saho Fujimoto, Sangita Karanjit, Kosuke Namba
Summary: The concise total synthesis of tronocarpine, a chippiine-type indole alkaloid, was achieved through a one-pot construction of a pentacyclic skeleton. This strategy, controlled by the stereocenter at the C14 position, can be used to synthesize other chippiine-type alkaloids with azabicyclo[3.3.1]nonane skeletons.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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
Hai-Hua Lu, Kang-Ji Gan, Fu-Qiang Ni, Zhihan Zhang, Yao Zhu
Summary: The concise total synthesis of salimabromide was achieved using a series of novel reactions, which allowed for the construction of its unique carbon skeleton and stereocenters.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(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
Lu Yang, Siwen Huang, Rongkang Huang, Anbin Hou, Sen Zhang, Hongwei Su, Xiaohong Ding, Bin Lin, Maosheng Cheng, Yongxiang Liu
Summary: The total syntheses of aspidospermidine and its derivatives were achieved from a common pentacyclic indoline intermediate through complex organic synthesis methods, providing an important foundation for further research on this class of indole alkaloids.
Article
Chemistry, Organic
Huan He, Fanglin Xue, Zhao Hu, Peng Li, Qian Xiao, Maojie Zhang, Fei Xue, Dan Zhang, Hao Song, Xiao-Yu Liu, Zhibing Zheng, Song Li, Wu Zhong, Yong Qin
Summary: Morphine and its related alkaloids are commonly used natural medicines. However, the current industrial manufacturing process of these compounds causes environmental issues. In this study, researchers developed an efficient total synthesis method for opioids such as codeine, oxycodone, naloxone, and naltrexone. The key step in this synthesis is the Pd-catalyzed dearomatization arene coupling reaction using an inexpensive and stable phosphonium ligand.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Gleb A. Chesnokov, Karl Gademann
Summary: The marine-derived compound Peyssonnoside A was successfully synthesized for the first time in a concise, efficient, scalable, and highly diastereoselective manner. The aglucone peyssonnosol was achieved in 21% overall yield after 15 steps, with key reactions including Simmons-Smith cyclopropanation and Mukaiyama hydration controlled by the spatial structure of the substrates.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Kristen M. Flynn, In-Soo Myeong, Taylor Pinto, Mohammad Movassaghi
Summary: We report the total synthesis of complex aspidosperma alkaloids (-)-voacinol and (-)-voacandimine C using a biogenetic hypothesis-inspired synthetic strategy. By chemoselective oxidation and methylenation reactions, we synthesized a versatile precursor that enabled the access to these natural alkaloids. The final-stage controlled reductive opening of a dodecacyclic intermediate led to a unified approach for the synthesis of (-)-voacinol and (-)-voacandimine C.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Meng-Yue Cao, Bin-Jie Ma, Qing-Xiu Gu, Bei Fu, Hai-Hua Lu
Summary: This paper reports a concise protecting-group-free total synthesis of Daphenylline, a structurally unique member of the triterpenoid Daphniphyllum natural alkaloids. Key reactions include an intramolecular oxidative dearomatization reaction, a tandem reductive amination/amidation double cyclization reaction, and a highly enantioselective rhodium-catalyzed hydrogenation reaction.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Hong-Gang Cheng, Zhenjie Yang, Ruiming Chen, Liming Cao, Wen-Yan Tong, Qiang Wei, Qingqing Wang, Chenggui Wu, Shuanglin Qu, Qianghui Zhou
Summary: A concise total synthesis of (-)-berkelic acid is reported in eight linear steps, featuring a Catellani reaction/oxa-Michael cascade, a one-pot deprotection/spiroacetalization operation, and a late-stage Ni-catalyzed reductive coupling. Notably, four stereocenters are established from a single existing chiral center with excellent stereocontrol during the deprotection/spiroacetalization process, supported by DFT calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Hosam Choi, Hanho Jang, Joohee Choi, Kiyoun Lee
Summary: This study presents an efficient approach for the synthesis of 4,5-disubstituted oxazolidin-2-one scaffolds, utilizing a combination of asymmetric aldol and modified Curtius protocol. The strategy allows for the rapid access to a range of oxazolidin-2-one building blocks, leading to the concise total synthesis of (-)-cytoxazone in just three steps. Ultimately, this convenient platform shows promise for early-stage drug discovery.
Article
Chemistry, Organic
Liu-Yang Pu, Zhiyue Li, Limin Li, Yucui Ma, Shengquan Hu, Zhengzhi Wu
Summary: In this study, we describe a concise and enantioselective total synthesis of isopavine alkaloids with a unique azabicyclo[3.2.2]nonane tetracyclic skeleton. Key steps include iridium-catalyzed asymmetric hydrogenation, Curtius rearrangement, and Eschweiler-Clarke methylation, enabling the synthesis of isopavine alkaloids in 6-7 linear steps. Additionally, we discovered that isopavine alkaloids, particularly (-)-reframidine (3), exhibit significant antiproliferative effects on various cancer cell lines for the first time.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Fuhao Zhang, Jingwen Zeng, Mohan Gao, Linzhou Wang, Gen-Qiang Chen, Yixin Lu, Xumu Zhang
Summary: A practical synthetic strategy for enantioselective and divergent synthesis of prostaglandins was reported, involving the construction of multiply substituted five-membered rings through key enyne cycloisomerization and installation of crucial chiral centers using asymmetric hydrogenation. Common intermediates allowed for the production of various prostaglandins and related drugs in two steps, with the preparation of fluprostenol on a 20-gram scale.
Article
Chemistry, Organic
Liu-Yang Pu, Zhiyue Li, Limin Li, Yucui Ma, Shengquan Hu, Zhengzhi Wu
Summary: We report a concise asymmetric total synthesis of isopavine alkaloids, which possess a unique azabicyclo[3.2.2]nonane tetracyclic skeleton. The key steps involve iridium-catalyzed asymmetric hydrogenation of unsaturated carboxylic acids, Curtius rearrangement, and Eschweiler-Clarke methylation, achieving an enantioselective approach to isopavine alkaloids in 6-7 linear steps. Moreover, isopavine alkaloids, especially (-)-reframidine (3), are found to exhibit effective antiproliferative effects on various cancer cell lines for the first time.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Emilia Oueis, Cyrille Sabot, Pierre-Yves Renard
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Organic
Kevin Renault, Cyrille Sabot, Pierre-Yves Renard
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Multidisciplinary
Kevin Renault, Laurie-Anne Jouanno, Antoine Lizzul-Jurse, Pierre-Yves Renard, Cyrille Sabot
CHEMISTRY-A EUROPEAN JOURNAL
(2016)
Review
Chemistry, Organic
Laurie-Anne Jouanno, Kevin Renault, Cyrille Sabot, Pierre-Yves Renard
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Hasan Mtiraoui, Rafik Gharbi, Moncef Msaddek, Yann Bretonniere, Chantal Andraud, Cyrille Sabot, Pierre-Yves Renard
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Antoine Lizzul-Jurse, Laetitia Bailly, Marie Hubert-Roux, Carlos Afonso, Pierre-Yves Renard, Cyrille Sabot
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Multidisciplinary
Hasan Mtiraoui, Rafik Gharbi, Moncef Msaddek, Yann Bretonniere, Chantal Andraud, Pierre-Yves Renard, Cyrille Sabot
Article
Chemistry, Multidisciplinary
Kevin Renault, Pierre-Yves Renard, Cyrille Sabot
NEW JOURNAL OF CHEMISTRY
(2017)
Article
Chemistry, Organic
Hasan Mtiraoui, Kevin Renault, Morgane Sanselme, Moncef Msaddek, Pierre-Yves Renard, Cyrille Sabot
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Chemistry, Organic
Mehdi Makrerougras, Romain Coffinier, Samuel Oger, Arnaud Chevalier, Cyrille Sabot, Xavier Franck
Review
Biochemical Research Methods
Kevin Renault, Jean Wilfried Fredy, Pierre-Yves Renard, Cyrille Sabot
BIOCONJUGATE CHEMISTRY
(2018)
Article
Chemistry, Organic
Kevin Renault, Pierre-Yves Renard, Cyrille Sabot
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Laurie-Anne Jouanno, Arnaud Chevalier, Nawal Sekkat, Nicolas Perzo, Helene Castel, Anthony Romieu, Norbert Lange, Cyrille Sabot, Pierre-Yves Renard
JOURNAL OF ORGANIC CHEMISTRY
(2014)
Editorial Material
Biochemistry & Molecular Biology
Cyrille Sabot, Peter Kele
Article
Chemistry, Multidisciplinary
Hasan Mtiraoui, Asma Nsira, Moncef Msaddek, Pierre-Yves Renard, Cyrille Sabot
COMPTES RENDUS CHIMIE
(2017)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)