Article
Chemistry, Organic
Thirupathi Reddy Penjarla, Adarash Kumar Shukla, Rituparna Hazra, Durba Roy, Maheshwar Kundarapu, Mudit Dixit, Anupam Bhattacharya
Summary: This article reports the synthesis of spiro compounds based on an indanedione-cyclopropane-pyrazolone framework. The reaction was carried out using the Michael-initiated ring closure strategy under Cu(OAc)(2) catalysis, assisted by an oxygen atmosphere and the base Et3N. The obtained compounds were mostly inseparable mixtures with modest to good yields using diverse substrates. Computational studies suggested that a route involving a four-membered Cu containing intermediate is feasible. The developed method has the potential to synthesize other analogous spiro systems.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
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
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, 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.
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
Chemistry, Physical
Valerio Sabatino, Dario Staub, Thomas R. Ward
Summary: The synthesis of N-substituted indoles via ring-closing metathesis of indole precursors with N-terminal alkenes was reported. Good yields (up to 72%) were achieved in aqueous metathesis using commercial catalysts or artificial metalloenzymes. Furthermore, the presence of a second metathesis substrate increased the yield of N-acetylindole.
Article
Chemistry, Organic
Luca Lizzadro, Oliver Spiess, Dieter Schinzer
Summary: A scalable and robust synthesis of (-)-disorazole C-1 with high stereoselectivity is described, featuring simple reaction conditions that can produce large quantities of this biologically active compound.
Article
Chemistry, Organic
Hinata Yokokawa, Seiya Ishizawa, Katsuya Saito, Yasuhiro Meguro, Shigefumi Kuwahara, Masaru Enomoto
Summary: The first total synthesis of aculene D, a structurally rare nordaucane-type natural product with quorum sensing inhibitory activity, was achieved. The synthesis involved nucleophilic addition, protection of a keto group, ring-closing metathesis, and additional manipulations. The synthesis of aculene D also resulted in the first total synthesis of aculene B through esterification with anN-protected L-proline followed by deprotection.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
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, Multidisciplinary
Nils Ansmann, Thaddaus Thorwart, Lutz Greb
Summary: The Lewis superacid bis(perchlorocatecholato)silane catalyzes C-O bond metathesis of alkyl ethers with high efficiency, enabling chemoselective ring contractions of macrocyclic crown ethers and unprecedented ring-closing metathesis of polyethylene glycols for polymer-selective degradation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
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.
