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)
Article
Chemistry, Multidisciplinary
Wei Cao, Zhen Wang, Yan Hao, Tianli Wang, Shaomin Fu, Bo Liu
Summary: We have achieved the total synthesis of sculponin U, a polycyclic C-20-oxygenated kaurane diterpenoid, through a radical cascade cyclization induced by photoinduced electron transfer (PET) of a silyl enolate. Our synthetic strategy involved a Diels-Alder reaction to form the middle six-membered ring and an iron-catalyzed hydrogen atom transfer to close the western cyclohexane ring. The successful preparation of enantiopure silyl enolate as the PET precursor allows for the asymmetric total synthesis of sculponin U and provides a new approach for the synthesis of structurally related compounds and pharmaceutical derivatives.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Zhuang Chen, Kuan Zhao, Yanxing Jia
Summary: This study presents a bioinspired total synthesis of (+)-euphorikanin A, which features a fascinating and intricate tetracyclic skeleton with a bridged [3.2.1]-gamma-lactone moiety. Key transformations involve stereoselective alkylation and aldol condensation to introduce the main stereocenters, an intramolecular nucleophile-catalyzed aldol lactonization of carboxylic acid-ketone to form the five-membered ring, a McMurry coupling to construct the seven-membered ring, and a biomimetic benzilic acid type rearrangement to generate the bridged [3.2.1]-gamma-lactone moiety.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Huy Tran, Guillaume Revol, Alyson Poyser, Louis Barriault
Summary: In this study, a novel Lewis acid gold catalyst was used to generate synthetically challenging polycyclic scaffolds through a one-pot cascade sequence. By controlling the ligand and reaction conditions, both 6,6,5-tricyclic and 6,6,6,5-tetracyclic cores were selectively synthesized in one operation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Bingnan Wang, Zhaobo Liu, Zhenzhong Tong, Beiling Gao, Hanfeng Ding
Summary: An electrochemical ODI-[5+2] cascade reaction has been developed for the rapid assembly of diversely functionalized bicyclo[3.2.1]octadienones from sensitive ethynylphenols. Through a combination of directed retro-aldol/aldol process, [2,3]-sigmatropic rearrangement, and Al(O-iPr)(3)-promoted reductive 1,3-transposition, the asymmetric total syntheses of five 8,9-seco-ent-kauranoids have been achieved in a concise and efficient manner.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Seema Dhiman, Johann F. Ulrich, Paul Wienecke, Thomas Wichard, Hans-Dieter Arndt
Summary: Chemical mediators play a crucial role in controlling symbiotic interactions in the environment. This study presents a fully stereoselective total synthesis of (-)-thallusin, a differentiation factor in algae, and shows its potent bioactivity in Ulva mutabilis. SAR investigations suggest that (-)-thallusin triggers different pathways in Ulva that can be separated by chemical editing of the compound structure.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Pragya Pali, Maya Shankar Singh
Summary: A simple and efficient domino strategy was developed for the synthesis of 1,2-dithioles using easily accessible dithioesters and aryl isothiocyanates. The reaction proceeded smoothly at room temperature without the need for a catalyst or additive, and produced high yields of 1,2-dithioles with diverse functional groups. The use of cheap and readily available reagents, O-2 as a green oxidant, and the ability for gram-scale synthesis are notable features of this approach. The formation of S-S bonds and cascade ring construction in this reaction were found to proceed through a radical pathway.
Article
Chemistry, Organic
Guanggen Liu, Zhijiang Zhang, Shaomin Fu, Bo Liu
Summary: The first asymmetric total synthesis of rumphellclovane E was accomplished in eight steps from commercially available (R)-carvone. Key elements of the synthesis included Rh-catalyzed cyclopropanation, iron-catalyzed intramolecular reductive aldol reaction, and SmI2-mediated chemo- and diastereoselective reduction of the cyclopentanone.
Article
Chemistry, Multidisciplinary
Niklas Rauscher, Line Noesborg, Christian Jandl, Thorsten Bach
Summary: In this study, the prezizane-type sesquiterpene agarozizanol B was synthesized through a photochemical cascade reaction, successfully achieving the key step of the synthesis with a specific strategy and obtaining the (+)-enantiomer that is identical to the natural product.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Nicole Hauser, Michael A. Imhof, Sarah S. Eichenberger, Tomas Kundig, Erick M. Carreira
Summary: The first total syntheses of the indole diterpenoids (+)-shearinine G and D were achieved through late-stage coupling, diastereoselective intramolecular cyclopropanation, Sharpless dihydroxylation/Achmatowicz reaction, and Prins cyclization. Tuning of the substituents on the parent arylcarboxaldehyde led to divergent products, further transformed into shearinines G and D, with unexpected stereochemical outcomes in the Riley-type oxidation of a bicyclic enone.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Ricardo I. Rodriguez, Leonardo Mollari, Jose Aleman
Summary: This study introduces a light-driven, atom-economical process for synthesizing enantiomerically enriched substituted chiral 1-pyrroline derivatives through distal functionalization of acyl heterocycles and the use of tailor-made ketimines as partners. Water is the sole by-product of the reaction, and stereoselectivity is controlled by coordination to a chiral-at-rhodium catalyst.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Caroline Poock, Markus Kalesse
Summary: The first total synthesis of halioxepine was achieved using 1,4-addition for constructing the quaternary center at C10 and halo etherification for generating the tertiary ether at C7. The correct structure of halioxepine was determined by assembling different enantiomeric building blocks and adjusting the relative configuration between C10 and C15.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Feng-Yuan Wang, Lei Jiao
Summary: An asymmetric total synthesis of cage-like indole alkaloid arborisidine is achieved using a new synthetic strategy that involves a catalytic parallel kinetic resolution based on ambident nucleophilicity of indole and a 5-exo-trig radical cyclization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Wei Chen, Zhun Feng, Qiang Liu
Summary: In this study, we reported the first stereoselective total synthesis of (1S,2S,4S)-beta-elemene and successfully synthesized it using a novel method. This accomplishment is of great significance for further biological investigations and the development of new antitumor drugs.
Article
Chemistry, Organic
Ryotaro Yagita, Kazuhiro Irie, Chihiro Tsukano
Summary: In this study, the left-hand fragment of Schinortriterpenoids, a class of complex and highly oxygenated polycyclic terpenes, was successfully synthesized with excellent diastereoselectivity through [3+2] cycloaddition. Computational studies were used to investigate the stereoselectivity, and further selective transformations resulted in a tricyclic skeleton with the desired stereochemistry.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kevin Hung, Matthew L. Condakes, Takahiro Morikawa, Thomas J. Maimone
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2016)
Article
Chemistry, Multidisciplinary
Yi-Hsiang Chen, Chih-Chun Lin, Min-Jie Huang, Kevin Hung, Yi-Ching Wu, Wei-Chieh Lin, Ren-Wu Chen-Cheng, Hao-Wu Lin, Chien-Hong Cheng
Article
Chemistry, Multidisciplinary
Matthew L. Condakes, Kevin Hung, Stephen J. Harwood, Thomas J. Maimone
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Applied
Chien-Hung Yeh, Yi-Chuen Lin, Subramaniyan Mannathan, Kevin Hung, Chien-Hong Cheng
ADVANCED SYNTHESIS & CATALYSIS
(2014)
Article
Chemistry, Multidisciplinary
Kevin Hung, Matthew L. Condakes, Luiz F. T. Novaes, Stephen J. Harwood, Takahiro Morikawa, Zhi Yang, Thomas J. Maimone
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Organic
Kevin Hung, Yugang Liu, Oliver Simon, Lei Zhang, Peichao Lu, Bryan K. S. Yeung, Christopher Sarko, Fumiaki Yokokawa