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, 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, 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
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, 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
Chemistry, Multidisciplinary
Lorenz E. Loeffler, Conny Wirtz, Alois Fuerstner
Summary: This paper presents a new approach to chemical synthesis that allows for the preparation of a variety of casbane derivatives, especially the more highly oxygenated and arguably more relevant members of the family. Key design elements include catalyst-controlled intramolecular cyclopropanation, chain extension of stereoisomeric cyclopropane building blocks, and ring-closing alkyne metathesis. The concise total syntheses of depressin, yuexiandajisu A, and ent-pekinenin C demonstrate the effectiveness of this method.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Andrew G. Dalling, Georg Spath, Alois Furstner
Summary: This article reports the first total synthesis of a tetracyclic marine pyridinium alkaloid, which was achieved using recent advances in chemoselectivity management. The synthesis involved the formation of critical C-C bond using nickel/iridium photoredox dual catalysis, successful ring closing alkyne metathesis (RCAM) despite the presence of a Lewis acidic alkylidyne catalyst, and a unique iridium catalyzed hydrosilylation reaction. The synthesis also demonstrated site- and chemoselective intramolecular N-alkylation for closing the second strained macrocycle.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Thomas Varlet, Soren Portmann, Alois Fuerstner
Summary: In this study, the first total synthesis of the cytotoxic marine natural product njaoamine C was achieved using double ring closing alkyne metathesis (dRCAM). Unlike previous approaches, both macrocyclic rings were formed simultaneously. The success of this synthesis was attributed to dynamic covalent chemistry and the chemoselectivity of palladium-catalyzed hydrostannation.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Maria Kourgiantaki, Vera P. Demertzidou, Alexandros L. Zografos
Summary: In this study, the oxy-Cope/ene reaction cascade was used to form a locked elemane conformer, enabling the short and scalable synthesis of versatile Apiaceae scaffolds. The divergent fate of the obtained macrocyclic germacrane was explored under different reaction conditions, leading to the diastereoselective synthesis of oxidized Apiaceae guaiane congeners and the total synthesis of 4-epi-epiguaidiol A. Additionally, the reduction of a hydrogen-bond-biased guaiane substrate allowed for the chemoselective synthesis of desoxo-jungiaguaiane.
Article
Chemistry, Organic
Paola Marzullo, Alice Maiocchi, Giuseppe Paladino, Umberto Ciriello, Leonardo Lo Presti, Daniele Passarella
Summary: The paper presents an enantioselective total synthesis of Cannabidiol-C-4, a natural product found in Cannabis extracts. The synthesis involves the use of 3,5-dimetoxybenzaldehyde as a starting material and includes several key steps such as Corey-Bakshi-Shibata reduction, Claisen-Ireland rearrangement, and ring-closing metathesis. The synthesized compound was characterized spectroscopically and confirmed to be present in low amounts in the extracts.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Felix Kaden, Peter Metz
Summary: In this study, the hydroazulene core of a bioactive sesquiterpenoid was generated by domino enediyne metathesis, with three out of four stereogenic centers of the target installed in a single step through a triple hydroboration/oxidation reaction. The enantiopure acyclic metathesis substrate was easily obtained via an asymmetric anti aldol reaction, and late-stage double carbonyl olefination was efficiently carried out after masking the gamma-lactone as an acetal.
Article
Chemistry, Multidisciplinary
Jake M. Aquilina, Myles W. Smith
Summary: We report the total synthesis of the Myrioneuron alkaloid myrioneurinol, which was enabled by recognizing the hidden symmetry within its polycyclic structure. By employing various strategic maneuvers, including the use of a chiral amine and a topologically controlled alkene hydrogenation, we achieved the first asymmetric synthesis of this target compound.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Ruben L. H. Andringa, Niels A. W. Kok, Arnold J. M. Driessen, Adriaan J. Minnaard
Summary: Ir-catalyzed asymmetric alkene hydrogenation combined with an established C-13-NMR method can effectively synthesize saturated isoprenoids and mycoketides, significantly improving synthetic efficiency.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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, Organic
Felix Kaden, Susanne Nowotni, Franziska Hoefner, Melanie Lorenz, Andre Barthel, Anne Jaeger, Felix Hennersdorf, Jan J. Weigand, Peter Metz
Summary: An efficient total synthesis of (-)-dehydrocostus lactone was achieved through a multi-step approach involving stereoselective reactions, hydroboration/oxidation, and olefination, significantly improving the efficiency of the synthesis process.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
