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
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
Hunter S. Sims, Pedro Andrade Horn, Ryota Isshiki, Melissa Lim, Yan Xu, Robert H. Grubbs, Mingji Dai
Summary: The concise and stereoselective total synthesis of the clinically relevant tricyclic prostaglandin D-2 metabolite methyl ester was achieved in eight steps using a variety of organic reactions. The synthesis also accumulated a significant amount of valuable material for clinical research purposes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Atsushi Nakayama, Tenta Nakamura, Toshihiro Zaima, Saho Fujimoto, Sangita Karanjit, Kosuke Namba
Summary: The concise total synthesis of tronocarpine, a chippiine-type indole alkaloid, was achieved through a one-pot construction of a pentacyclic skeleton. This strategy, controlled by the stereocenter at the C14 position, can be used to synthesize other chippiine-type alkaloids with azabicyclo[3.3.1]nonane skeletons.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Hai-Hua Lu, Kang-Ji Gan, Fu-Qiang Ni, Zhihan Zhang, Yao Zhu
Summary: The concise total synthesis of salimabromide was achieved using a series of novel reactions, which allowed for the construction of its unique carbon skeleton and stereocenters.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
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, 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
Gleb A. Chesnokov, Karl Gademann
Summary: The marine-derived compound Peyssonnoside A was successfully synthesized for the first time in a concise, efficient, scalable, and highly diastereoselective manner. The aglucone peyssonnosol was achieved in 21% overall yield after 15 steps, with key reactions including Simmons-Smith cyclopropanation and Mukaiyama hydration controlled by the spatial structure of the substrates.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
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)
Review
Chemistry, Multidisciplinary
Long Min, Li-Ping Zhong, Chuang-Chuang Li
Summary: Steroids continue to play a significant role in organic chemistry, medicinal chemistry, and drug discovery. However, the synthesis of unusual rearranged steroids, particularly abeo-steroids with a medium-sized ring, remains a challenge. This Account summarizes the laboratory's efforts in the total synthesis of abeo-steroids using cycloaddition strategies, highlighting the efficiency and versatility of each strategy in constructing structurally complex abeo-steroid cores. The findings provide valuable insights for advancing the total synthesis of abeo- and related steroids.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Organic
Huan He, Fanglin Xue, Zhao Hu, Peng Li, Qian Xiao, Maojie Zhang, Fei Xue, Dan Zhang, Hao Song, Xiao-Yu Liu, Zhibing Zheng, Song Li, Wu Zhong, Yong Qin
Summary: Morphine and its related alkaloids are commonly used natural medicines. However, the current industrial manufacturing process of these compounds causes environmental issues. In this study, researchers developed an efficient total synthesis method for opioids such as codeine, oxycodone, naloxone, and naltrexone. The key step in this synthesis is the Pd-catalyzed dearomatization arene coupling reaction using an inexpensive and stable phosphonium ligand.
ORGANIC CHEMISTRY FRONTIERS
(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, Multidisciplinary
Hong-Gang Cheng, Zhenjie Yang, Ruiming Chen, Liming Cao, Wen-Yan Tong, Qiang Wei, Qingqing Wang, Chenggui Wu, Shuanglin Qu, Qianghui Zhou
Summary: A concise total synthesis of (-)-berkelic acid is reported in eight linear steps, featuring a Catellani reaction/oxa-Michael cascade, a one-pot deprotection/spiroacetalization operation, and a late-stage Ni-catalyzed reductive coupling. Notably, four stereocenters are established from a single existing chiral center with excellent stereocontrol during the deprotection/spiroacetalization process, supported by DFT calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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
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)
