Article
Chemistry, Organic
Somsuvra Banerjee, Takafumi Kobayashi, Kazuhiko Takai, Sobi Asako, Laurean Ilies
Summary: In the presence of triphenylphosphine as a mild reductant, the use of catalytic amounts of Mo(CO)6 and an ortho-quinone ligand enables the intermolecular reductive coupling of aromatic aldehydes and the intramolecular coupling of aromatic ketones to produce functionalized alkenes. Diaryl-and diheteroaryl alkenes are synthesized with high (E)-selectivity and a tolerance toward bromide, iodide, and steric hindrance. Intramolecular coupling of dicarbonyl compounds under similar conditions affords mono-and disubstituted phenanthrenes.
Article
Chemistry, Multidisciplinary
Yusuke Imamura, Kyohei Takaoka, Yuma Komori, Masanori Nagatomo, Masayuki Inoue
Summary: This study presents a 34-step synthesis of Taxol, involving inter- and intramolecular radical reactions to connect the A- and C-ring fragments and cyclize the B-ring. The A- and C-ring functional groups were then efficiently modified using newly developed selective reactions. The construction of the D-ring and its conjugation with the beta-amino acid led to the successful synthesis of Taxol. This synthesis provides useful insights for the design of multistep syntheses of diverse bioactive natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Inorganic & Nuclear
Vladimir B. Kharitonov, Dmitry V. V. Muratov, Dmitry A. Loginov
Summary: This review comprehensively summarizes the use of cyclopentadienyl complexes of Group 9 metals in the total synthesis of natural compounds, including catalyzing cycloaddition, transfer hydrogenation, and C-H activation reactions.
COORDINATION CHEMISTRY REVIEWS
(2022)
Review
Chemistry, Multidisciplinary
Jiawei Sun, He Yang, Wenjun Tang
Summary: This tutorial review summarizes the total synthesis of complex dimeric natural products and discusses various dimerization strategies. By highlighting selected representative examples, it aims to demonstrate the recent tactics of dimerization and provide insights on structural and chemical properties of related natural products, promoting advancements in organic synthesis and biological studies.
CHEMICAL SOCIETY REVIEWS
(2021)
Review
Chemistry, Multidisciplinary
Debobrata Paul, Ashis Kundu, Sanu Saha, Rajib Kumar Goswami
Summary: This feature article highlights total synthesis as a reliable tool for confirming the structure of natural products. Despite advances in spectroscopic techniques, structural misassignments of natural products remain common. Recent case studies have shown that chemical synthesis can be used to revise the structures of natural products.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Jin-Tao Ma, Tianze Zhang, Bo-Ying Yao, Li-Jun Xiao, Qi-Lin Zhou
Summary: We present a enantioselective nickel-catalyzed borylative coupling of 1,3-dienes with aldehydes, providing a one-step efficient synthesis of highly valuable homoallylic alcohols. The reaction involves 1,4-carboboration of dienes leading to the formation of C-C and C-B bonds and the construction of two continuous stereogenic centers. The diastereoselectivity of the reaction can be controlled by the choice of (Z)-1,3-dienes or (E)-1,3-dienes.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Xikang Zheng, Yan Li, Mengtie Guan, Lingyue Wang, Shilong Wei, Yi-Cheng Li, Chin-Yuan Chang, Zhengren Xu
Summary: A unified strategy for the biomimetic total synthesis of the spiroindimicin family of natural products was reported. Key transformations include one-pot two-enzyme-catalyzed oxidative dimerization and regioselective bond formation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Zhen Yang
Summary: The total synthesis endeavors contribute to the discovery and invention of new synthetic reactions to advance organic synthesis. Bioactive compounds share common features, such as molecular complexity, protein-binding ability, structural rigidity, and three-dimensionality. Total synthesis offers an alternative solution for generating scarce natural products and their derivatives for studying their biological functions.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Review
Chemistry, Multidisciplinary
Huilin Li, Jing Zhang, Xuegong She
Summary: This MiniReview demonstrates the achievements in the construction of the diquinane ring system in the past decade, discussing the strategic synthesis of the diquinane unit and its impact on the field of natural product total synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Haoran Dong, Dachao Hu, Benke Hong, Jin Wang, Xiaoguang Lei
Summary: The first total syntheses of four natural antibiotics, vermisporin, PF1052/AB4015-A, AB4015-L, AB4015-B, and one hydrogenated natural product derivative, AB4015-A2, featuring a tetramic acid bearing cis-decalin ring, are reported. The functionalized cis-decalin ring was constructed via a diastereoselective intramolecular Diels-Alder (IMDA) reaction, with a rare endo-boat transition state. The efficient installation of the sterically hindered epoxy group in vermisporin, PF1052/AB4015-A, and AB4015-L was achieved through an intramolecular neighboring-group-oriented strategy, and the desired tetramic acid structure was obtained through a one-pot aminolysis/Dieckmann condensation cascade using L-amino acid derivatives. The total synthesis allowed for the unequivocal verification of the absolute configuration of these natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Xinyi Li, Long Liu, Tianzeng Huang, Zhi Tang, Chunya Li, Wenhui Li, Tao Zhang, Zhaohui Li, Tieqiao Chen
Summary: A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis without the use of excess oxidants, providing a relatively general method for preparing internal alkynes.
Review
Electrochemistry
Chad E. Hatch, William J. Chain
Summary: Electrochemical techniques have played a crucial role in the total synthesis of natural products since the pioneering work of Kolbe in the mid 1800s. These techniques have expanded over time, changing the way chemists approach and think about natural products. This review provides a perspective on the use of electrochemical techniques in enabling carbon-carbon bond formations in the assembly of important natural products, discussing mechanistic details and showcasing representative examples from the past few decades. These bond formations offer unique possibilities compared to conventional chemistries, allowing for complementary synthetic strategies.
Review
Chemistry, Organic
Takaaki Sato, Takahiro Suto, Yoshiyuki Nagashima, Shori Mukai, Noritaka Chida
Summary: Skipped dienes, found in various biologically active natural products, have relatively undeveloped synthesis methods compared to conjugated dienes due to challenges posed by the sp(3)-hybridized carbon between two olefins. Recent advances in the synthesis of skipped dienes for total synthesis of complex natural products are classified into three categories, focusing on methods to achieve both high stereoselectivity and convergency.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yuuki Watanabe, Hisahiro Morozumi, Hiroyuki Mutoh, Koichi Hagiwara, Masayuki Inoue
Summary: In this study, a total synthesis of batrachotoxin was achieved using a newly devised convergent strategy. The researchers successfully prepared enantiopure fragments of the AB-ring and D-ring, and connected them through a crucial C(sp(2))-C(sp(2)) coupling reaction. By optimizing the functionalizations, the team realized the formation of oxazepane, carbon chain extension, and pyrrole carboxylic acid condensation to deliver batrachotoxin.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Biochemistry & Molecular Biology
Matthew C. Carson, Marisa C. Kozlowski
Summary: Covering the period from 2008 to 2023, this review examines the use of oxidative phenol coupling in the total synthesis of natural products. The review explores catalytic and electrochemical methods, comparing them to stoichiometric and enzymatic systems in terms of practicality, atom economy, and other factors. It also discusses the synthesis of natural products through C-C and C-O oxidative phenol couplings, as well as alkenyl phenol couplings. Additionally, the review surveys the catalytic oxidative coupling of phenols and other related species, such as carbazoles, indoles, and aryl ethers. Future research directions in this field are also assessed.
NATURAL PRODUCT REPORTS
(2023)
Article
Chemistry, Organic
Robert K. Orr, Louis-Charles Campeau, Harry R. Chobanian, Jamie M. McCabe Dunn, Barbara Pio, Christopher W. Plummer, Andrew Nolting, Rebecca T. Ruck
SYNTHESIS-STUTTGART
(2017)
Article
Chemistry, Multidisciplinary
Jamie M. McCabe Dunn, Mikhail Reibarkh, Edward C. Sherer, Robert K. Orr, Rebecca T. Ruck, Bryon Simmons, Ana Bellomo
Article
Chemistry, Multidisciplinary
Robert K. Orr, Jamie M. McCabe Dunn, Andrew Nolting, Alan M. Hyde, Eric R. Ashley, Joseph Leone, Eric Sirota, Jon A. Jurica, Andrew Gibson, Christopher Wise, Steven Oliver, Rebecca T. Ruck
Article
Chemistry, Applied
Jamie M. McCabe Dunn, Alicia Duran-Capece, Brendan Meehan, James Ulis, Tetsuo Iwama, Guy Gloor, George Wong, Evan Bekos
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2011)
Article
Chemistry, Applied
Lijun Wang, Leopold Green, Zhen Li, Jamie McCabe Dunn, Xiaodong Bu, Christopher J. Welch, Chunyu Li, Tiebang Wang, Qiang Tu, Evan Bekos, Douglas Richardson, Jeffrey Eckert, Jian Cui
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2011)
Article
Chemistry, Applied
Susan L. Zultanski, Nadine Kuhl, Wendy Zhong, Ryan D. Cohen, Mikhail Reibarkh, Jon Jurica, Jungchul Kim, Lauren Weisel, Anil R. Ekkati, Artis Klapars, Donald R. Gauthier, Jamie M. McCabe Dunn
Summary: The study investigated the mechanism of perfunctionalization reactions of cyclodextrin, introducing a simple acidic hydrolytic quench method to replace the traditional strongly basic quenching step. This method not only allows quantification and removal of HX in the reaction solution but also facilitates the identification of sensitive intermediates and byproducts during the reaction process and optimization of reaction conditions. Through high-throughput experimentation, the new acidic quench method proved to be effective in understanding the complex effects of Vilsmeier equivalents and temperature on the reaction outcome.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Organic
Kay M. Brummond, Jamie M. McCabe
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.
