Article
Chemistry, Organic
Frank Schmidt, Aparna Viswanathan Ammanath, Friedrich Goetz, Martin E. Maier
Summary: A new synthesis route was established for the macrolactone antibiotic berkeleylactone A. The synthesis involved ring-closing alkyne metathesis (RCAM) of an ester substrate with 1-propynyl termini. The carboxylic part of the substrate was assembled using alkyne chemistry, while the alcohol part of the ester was synthesized through propylene oxide opening and triple bond migration reactions. After successful RCAM, the triple bond was selectively hydrogenated and the 4,5-diol was oxidized to obtain the desired derivative. The thioether formation and reduction of the 8,9-double bond were also achieved. However, the antimicrobial activity of the analog was found to be slightly reduced.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sambasivarao Kotha, Deepshikha Singh, Vijayalakshmi Bandi
Summary: An efficient and short synthetic sequence for highly functionalized urazole derivatives has been reported. N-substituted-1,2,4-triazoline-3,5-dione (TAD) was used as a versatile synthetic reagent. Simple reactions including allylation, ring-closing metathesis, and hydrogenation were successfully employed to construct oxygenated urazole derivatives, which may have implications in medicinal chemistry and organic synthesis.
Article
Polymer Science
Yujin Cha, JiHyeon Hwang, Luis Ramos, Huina Lin, Tianyu Zhu, Chuanbing Tang
Summary: The synthesis of cyclic cobaltocenium and its application in the synthesis of high-performance copolymers have been reported.
Review
Chemistry, Organic
Waqar Ahmed, Vikrant Jayant, Shakeel Alvi, Nadeem Ahmed, Azeem Ahmed, Rashid Ali
Summary: The synthesis of natural products has always been a top priority for synthetic chemists worldwide. Various synthetic methodologies have been used to extract, elucidate, synthesize, and document a wide range of natural products. The synthesis of complex natural products often presents challenges that can be overcome through modification or development of new synthetic methods. Metathesis tactics, discovered unexpectedly in the 1950s and awarded the Nobel Prize in 2005, have greatly influenced and changed the landscape of total and formal synthesis. This review article provides a comprehensive detail of metathetic tools used in the synthesis of natural products from 2017 to 2019.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Fatema Jagot, Songeziwe Ntsimango, Kennedy J. Ngwira, Manuel A. Fernandes, Charles B. de Koning
Summary: This article describes the key steps in the synthesis of derivatives of angucycline, tetrangulol, including the catalyzed SuzukiMiyaura cross-coupling reaction, iron-catalyzed ring-closing carbonyl-olefin metathesis reaction, and late-stage oxidation reaction. The chlorinated compounds were obtained as final products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Ervin Kovacs, Bence Balterer, Nguyen Anh Duc, Gyorgyi Szarka, Michael C. Owen, Attila Domjan, Bela Ivan
Summary: A large number of organic solvents contaminate the environment on a daily basis worldwide. This study demonstrates that benzotrifluoride can be used as a suitable solvent for olefin metathesis reactions, providing high yields and similar or even higher reaction rates compared to dichloromethane.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Qiaoqiao Ao, Hai-Jun Zhang, Jinbin Zheng, Xiaoming Chen, Hongbin Zhai
Summary: The first asymmetric total synthesis of (+)-Mannolide C has been achieved through key transformations such as lipase-mediated resolution, Ru-complex-catalyzed double ring-closing metathesis (RCM) reactions, Ni-II-catalyzed diastereoselective Michael addition, and Mn-III-catalyzed allylic oxidation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Damien F. Dewez, Christina Diacofotaki, Gwilherm Evano
Summary: A new class of nitrogen-containing heterocycles featuring both a cyanamide and an unsaturated ring can be readily obtained through ring-closing metathesis. These compounds have potential applications in drug discovery and can serve as building blocks. The presence of the endocyclic double bond provides a useful access to novel polycyclic heterocycles.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Biochemistry & Molecular Biology
Anna Brodzka, Dominik Koszelewski, Ryszard Ostaszewski
Summary: The goal of diversity-oriented synthesis is to achieve structural diversity of compounds, but issues with low efficiency and multiple purification steps in kinetic resolution exist. A new concept has been proposed to simultaneously form two skeletally and enantiomerically diverse platform molecules in a one-pot protocol to overcome these limitations.
Article
Chemistry, Organic
Gihan C. Dissanayake, Cornelius N. Ndi, Jana L. Markley, James B. Martinez, Paul R. Hanson
Summary: Two synthetic strategies involving phosphate tether-mediated one-pot sequential protocols were developed for the total synthesis of sanctolide A, a polyketide nonribosomal peptide macrolide, and the formal synthesis of its (2S)-epimer.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sambasivarao Kotha, Balaji U. Solanke
Summary: This article describes an easy-to-execute strategy for synthesizing benzofurans, 2H-chromenes, and benzoxepines using Claisen rearrangement and ring-closing metathesis as key steps, and includes examples of natural products and pharmaceuticals containing these structural elements.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Review
Chemistry, Organic
Santhosh Kumar Podiyanachari, Hassan S. Bazzi, Mohammed Al-Hashimi
Summary: Synthesis of cycloolefin-based polymers via metathesis-accompanied cyclopolymerization and tandem ring-opening/ring-closing metathesis (RO/RCM) polymerization leads to highly functional cycloolefin ring-based polymers.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Andrea Ojeda-Porras, Remi Aouzal, Claire Wilson, Joelle Prunet
Summary: Two synthetic routes for the ABC tricycle of Taxol are presented, both involving a relay ring-closing metathesis reaction to form the central B ring. In the first approach, the extender arm is positioned on the A ring, while the C ring bears the relay tether in the second route. Despite the efficient synthesis of metathesis precursors with diverse extender arms, the crucial metathesis reactions failed to yield the target compounds in all cases.
Article
Chemistry, Multidisciplinary
Sambasivarao Kotha, Balaji U. U. Solanke
Summary: This article presents an easy-to-execute strategy for the synthesis of benzofurans and benzoxepines using Claisen rearrangement and ring-closing metathesis. The compounds synthesized through this method are important for drug development and the design of natural products.
Article
Chemistry, Multidisciplinary
Sambasivarao Kotha, Balaji U. Solanke
Summary: We present a novel approach to a library of multidimensional O-heterocycles based on a rigid, tetrahedral core. New derivatives of tetraphenylmethane (TPM) were synthesized using Claisen rearrangement (CR) and ring-closing metathesis (RCM). These compounds include mono-, di-, tri-, and tetra-substituted benzofurans, 2H-chromenes, and benzoxepine derivatives. The incorporation of various heterocyclic cores, commonly found in natural products and pharmaceuticals, as well as the versatility of the tetrahedral framework make this approach significant for the construction of complex molecules. The synthesis of five-, six-, and seven-membered O-heterocycles in the TPM core, along with the base-catalyzed inexpensive synthesis of isomerized intermediates, represents important advancements in the field.
