Article
Chemistry, Organic
Philip Koblischek, Reinhard Brueckner
Summary: This study describes another total synthesis of aurantricholone, reaching its core structure through known olefin metathesis products and dibromide compounds. By optimizing the reaction conditions, the study successfully avoids the forcing hydrolysis required in traditional synthesis methods and analyzes the structure of the product in detail.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
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, Multidisciplinary
Lian-Dong Guo, Zejun Xu, Rongbiao Tong
Summary: The asymmetric total syntheses of three paspaline-derived IDTs were reported, featuring green Achmatowicz rearrangement/bicycloketalization and cascade ring-closing metathesis of dienyne, as well as four palladium-mediated reactions. These synthetic strategies are expected to facilitate the chemical synthesis of other paspaline-derived IDTs and further bioactivity studies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Adisak Thanetchaiyakup, Hassayaporn Rattanarat, Sudaporn Aree, Tanwawan Duangthongyou, Tanin Nanok, Nutthawat Chuanopparat, Paiboon Ngernmeesri
Summary: Melotenine A, derived from Melodinus tenuicaudatus, shows significant anticancer activity against several human cancer cell lines. The synthesis of (+/-)-melotenine A was achieved in 11 steps with an overall yield of 6.7%, using key steps including a Diels-Alder reaction and ring-closing metathesis.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Yuan Jin, Kensuke Orihara, Fumiki Kawagishi, Tatsuya Toma, Tohru Fukuyama, Satoshi Yokoshima
Summary: The total synthesis of Haliclonin A was achieved through a series of reactions including Birch reduction/alkylation, ring-closing metathesis, intramolecular cyclopropanation, and stereoselective 1,4-addition, leading to the formation of the desired compound.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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
David Kieslich, Jens Christoffers
Summary: The first total synthesis of racemic chebulic acid from the fruit of the Terminalia chebula tree has been reported. The overall synthetic route consists of nine consecutive steps and was accomplished in 15% overall yield.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
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
Saskia Schulthoff, James Y. Hamilton, Marc Heinrich, Yonghoon Kwon, Conny Wirtz, Alois Furstner
Summary: This article describes how total synthesis was used to confirm and assign the structure of cytotoxic marine macrolides, and discusses the use of modular design and catalyst-controlled transformations to achieve the preparation of stereo isomers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Plant Sciences
Jiahui Lin, Zihao Zhu, Yuwen Chen, Weiwei Zuo, Meifang Zhu, Zhiyuan Ma
Summary: The combination of ring-closing metathesis with betulin allows for the synthesis of a library of triterpenoid derivatives for potential pharmacological research. Different types of betulin derivatives were prepared by coupling reactions and subsequent ring-closing metathesis. The resulting betulin-based olefin derivatives showed potential applications in the biomedical field.
JOURNAL OF NATURAL PRODUCTS
(2023)
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, 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
Yecai Lai, Wei-Min Dai
Summary: A pentamodule assembly approach has been developed for the total synthesis of (-)-palmyrolide A and (+)-5,7-epi-palmyrolide A. The flexibility of the multimodule assembly strategy for diverted total synthesis is demonstrated by the ability to obtain two diastereoisomeric macrolides from the same sequence of reactions.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Myron Triantafyllakis, Sam Alexander, Sophie Woolford, Claire Wilson, J. Stephen Clark
Summary: The fully functionalized A-F fragment of the Pacific ciguatoxin CTX3C has been synthesized using specific reaction sequences and synthesis routes, achieving the construction of a multi-ring system and the introduction of functional groups.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Polymer Science
Mohammad Yasir, Andreas F. M. Kilbinger
Summary: Norbornene and cyclohexene show different polymerization behaviors using Grubbs' catalysts due to their varying ring strain energy levels; a sequence-selective cascade polymerization of a monomer containing both rings resulted in polymers with moderate molecular weight dispersities and good control over molecular weight.
