Article
Chemistry, Multidisciplinary
Jinlei Wang, Xingwei Li
Summary: The precise control of multiple chiral elements through a single step catalytic process remains a significant challenge in asymmetric catalysis. Reported herein is rhodium-catalyzed three-component asymmetric carboamidation between aryl boronic acid, achiral strain-activated symmetric bicyclic olefins bearing a prochiral C-N or N-N axis, and dioxazolones. The reaction proceeded effectively in excellent enantio- and diastereoselectivity under mild conditions to produce the bicyclic framework with six contiguous chiral centers as well as a N-N or C-N chiral axis. The reaction featured excellent functional group tolerance, chemoselectivity, and stereoselectivity. Mechanistic studies indicated that the coupling system proceeded via initial transmetalation, followed by stereo-determining migratory insertion into the olefin and electrophilic amidation.
SCIENCE CHINA-CHEMISTRY
(2023)
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, Organic
Caroline G. Webster, Hyeri Park, Amanda F. Ennis, Jiyong Hong
Summary: Rhodojaponin III is a natural product with a novel chemical scaffold and potent antinociceptive activity, potentially representing a new class of natural non-opioid analgesics. Researchers synthesized the bicyclo[3.2.1]octane fragment of this compound through Au(I) and Mn(III)-mediated reactions, providing important experimental tools for future biological studies.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Ismaila Ciss, Matar Seck, Bruno Figadere, Laurent Ferrie
Summary: Amphidinolide U is a cytotoxic marine macrolide isolated from Amphidinium sp., and it shares 75% similarity in backbone with amphidinolide C. In this study, we report the synthetic study of the C-1-C-12 fragment of amphidinolide U. The C-6-C-12 pattern was constructed using consecutive regioselective ring opening of epoxides, while the C-1-C-5 moiety was built using a symmetrical diol. Attempts to cross-couple the C-1-C-5 and C-6-C-12 fragments through Suzuki cross-coupling reaction resulted in poor conversion rates, possibly due to steric hindrance of the protecting group adjacent to the vinyl function.
Review
Chemistry, Medicinal
Wesam S. Shehab, Mostafa M. K. Amer, Doaa A. Elsayed, Krishna Kumar Yadav, Magda H. Abdellattif
Summary: This mini-review article focuses on the synthetic approaches and medicinal importance of quinoline and its analogs, emphasizing the use of green and sustainable chemical processes as well as the pharmacophore class of quinoline in various therapeutic agents.
MEDICINAL CHEMISTRY RESEARCH
(2023)
Article
Environmental Sciences
Yaya Feng, Chunlin Huang, Xiaoyu Song, Juan Gu
Summary: This study calculated the integrated index of SDG 11 at prefecture-level cities in the Yellow River Basin using Big Earth Data and statistical data. Spatial aggregation characteristics and synergies and trade-offs among indicators were analyzed. The results showed overall improvement in the integrated index and indicators from 2015 to 2020, with variations between different economic groups. The study also identified indicators that require attention and provided a foundation for implementing the 2030 Agenda for Sustainable Development.
Article
Chemistry, Multidisciplinary
Takayuki Ohyoshi, Hikaru Tano, Hideo Kigoshi
Summary: The synthesis of Aplysiasecosterol A involves pseudo-desymmetrizing acetalization and acyl radical cyclization to construct the unique tricyclic core. An efficient method for introducing the D ring fragment was developed using an organocuprate, advancing the total synthesis process.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2021)
Article
Chemistry, Organic
Qi-Kai Kang, Hang Shi
Summary: Introducing deuterium and tritium into molecules is crucial for drug discovery. Recent advancements in catalytic HIE reactions have provided efficient methods for late-stage labeling of bioactive complex molecules and pharmaceuticals, avoiding multistep syntheses.
Article
Chemistry, Organic
Feng-Xia Li, Qing-Zhou Zhang, Shi-Jun Li, Guang Lin, Xiang-Yu Huo, Yu Lan, Zhen Yang
Summary: CRV431, a non-immune-suppressive cyclophilin inhibitor, is a clinical candidate for treating NASH and shows potential in treating liver fibrosis and cancer. The compound was synthesized in four steps from commercially available cyclosporine using various chemical reactions.
Article
Chemistry, Multidisciplinary
Kai Chen, Qi-Kai Kang, Yuntong Li, Wen-Qiang Wu, Hui Zhu, Hang Shi
Summary: This study describes a rhodium-catalyzed amination of phenols, providing a concise method for the synthesis of diverse anilines with no byproduct. The use of an arenophilic rhodium catalyst enables the challenging keto-enol tautomerization of phenols and subsequent condensation with amines. The generality of this redox-neutral catalysis is demonstrated through reactions with various phenols and amines, showcasing the potential broad utility of the method, including late-stage functionalization of structurally complex bioactive molecules.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Jun Huang, Tingting Cao, Zhongchao Zhang, Zhen Yang
Summary: The article describes an enantioselective semisynthesis of (-)-bufospirostenin A, involving the use of biomimetic and diastereoselective reactions for construction of the bicyclic motif, and a Co-catalyzed reversible double-bond isomerization reaction for installing the double bond.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Tingting Cao, Lei Zhu, Jun Huang, Zhen Yang
Summary: This study successfully installed a sterically congested all-carbon quaternary center for the first time via a Pd-catalyzed cascade diarylation, providing a new method for the synthesis of complex organic compounds.
Article
Chemistry, Organic
Lijie Zhang, Rongya Wang, Chao Wang, Bingyan Liu, Jinfeng Yang, Zhongchao Zhang, Jun Huang, Zhen Yang
Summary: A spiro-oxepin isoxazoline skeleton was synthesized via 1,3-dipole cycloaddition, enabling the total syntheses of 7-deoxyceratinamide A and 7-deoxypsammaplysins K and O.
Article
Chemistry, Organic
Jia-Yue Li, Lun Li, Yun-Zhi Lin, Hang Shi
Summary: Allylic amines were synthesized through a nickel-catalyzed coupling reaction. The method is free of additional oxidant/reductant or activating reagent and avoids the use of external ligands, improving its atom economy.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Yuntong Li, Wen-Qiang Wu, Hui Zhu, Qi-Kai Kang, Lun Xu, Hang Shi
Summary: In this study, we report Rh-catalyzed benzylic addition of alkylarenes to Michael acceptors, which involves the activation of the aromatic ring for deprotonation of the unactivated benzylic C-H bond and addition of the resulting carbanion to the α,β-unsaturated double bond. This byproduct-free method provides access to all-carbon quaternary centers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yuan-He Li, Su-Lei Zhang, Yong Lu, Bo Xiao, Tian-Yu Sun, Qian-Qian Xu, Jia-Hua Chen, Zhen Yang
Summary: A highly enantioselective catalytic system for exo-Diels-Alder reactions was developed using bispyrrolidine diboronates(BPDB). Activated by various Lewis or Bronsted acids, BPDB can catalyze highly stereoselective asymmetric exo-Diels-Alder reactions. The catalyst can also distinguish between different binding sites to achieve highly regioselective reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jiang Su, Kai Chen, Qi-Kai Kang, Hang Shi
Summary: We describe a rhodium-catalyzed nucleophilic aromatic substitution of aryl chlorides or bromides with weakly nucleophilic hexafluoro-2-propanol. This method provides diverse hexafluoroisopropyl aryl ethers and relies on arene activation by means of ?(6)-coordination.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Shu-Min Lu, Chao Chen, Chang Liu, Rudong Liu, Jia-Hua Chen, Zhongchao Zhang, Zhen Yang
Summary: Regioselective synthesis of 5,6,7-trihydroxyl and 5,7,8-trihydroxyl flavones was achieved using a transition-metal-catalyzed C-H oxidation with naturally enriched 5,7-dihydroxyl flavone as the starting material. This method was applied to the synthesis of biologically active flavonoids wogonin, oroxylin A, and their glycosylated derivatives as potential carnitine palmitoyltransferase 1 activators.
Article
Multidisciplinary Sciences
Ke Li, Wen-Qiang Wu, Yunzhi Lin, Hang Shi
Summary: The authors demonstrate a relay strategy for constructing compounds with a chiral gem-diaryl carbon center through selective arene exchange and asymmetric hydrogenation. This strategy involves the selective arene exchange between 1,1-diarylethylenes or benzophenones with (naphthalene)Cr(CO)3, followed by asymmetric hydrogenation. Differentiating the prochiral faces of a double bond is challenging for hydrogenation catalysts.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Hao-Yuan Liu, Zhen-Yu Zhang, Yi-Ke Zhou, Jia-Hua Chen, Zhen Yang, Yuan-He Li
Summary: This paper presents an efficient strategy for synthesizing the DEFGH rings of phainanoid F, involving a photo-induced electrocyclization and a homoallylic elimination. It is noteworthy that the electrocyclization reaction was used to simultaneously construct two vicinal quaternary carbons in total synthesis, which is a rare example. The strategy outlined here serves as the basis for the total synthesis of Phainanoid F and could be applied in synthesizing other natural products with similar 13,30-cyclodammarane skeletons.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Zhenyu Zhang, Wei Zhang, Jun-Chen Tang, Jin-Teng Che, Zhongchao Zhang, Jia-Hua Chen, Zhen Yang
Summary: The researchers synthesized (+)-Haperforin G in 20 steps from commercially available starting materials. They used a Co-catalyzed intramolecular Pauson-Khand reaction to selectively construct a cyclopentanone with an all-carbon quaternary stereogenic center at the bridge-head position. Light-initiated photocatalysis was employed for the convergent and asymmetric cross-coupling of the unstabilized C(sp(3)) radical with an enone. This developed chemistry opens up possibilities for synthesizing structurally diverse analogs of haperforin G (6).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Wen-Qiang Wu, Hang Shi
Summary: This review summarizes recent advances in the transition-metal-catalyzed dehydrogenative (3 + 2) annulation of aromatic hydrocarbons, which involves the fusion of two distinct components to construct 5-membered carbocycles through the dual functionalization of benzylic and ortho C-H bonds.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
