Article
Chemistry, Multidisciplinary
Atefeh Moshtari-Sarand, Shabnam Rahimpour, Reza Teimouri-Mofrad
Summary: In this study, 5,6-dimethoxy-2-methylene-2,3-dihydro-1H-inden-1-one was synthesized by evaluating old methods and examining new methods. alpha-beta unsaturated derivatives of 5,6-dimethoxy-1-indanone were reacted with various nucleophiles under Michael addition reaction condition, resulting in compounds with different stability. The possibility of retro-Michael reaction was also examined. The synthesized 1-indanone derivatives played a crucial role in the progress of this reaction, with aliphatic amines showing more tendency for retro-Michael reaction compared to aromatic amines.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Sadhanendu Samanta, Jin Cui, Hidetoshi Noda, Takumi Watanabe, Masakatsu Shibasaki
Summary: In this study, a gram-scale syn-selective asymmetric vinylogous addition of butenolides to chromones was developed using an Al-Li-BINOL (ALB) complex catalyst. The reaction showed high diastereoselectivity with ratios up to 20:1 and enantioselectivity of 84-98% for various substrate combinations. This method is complementary to previous reports and improves selectivity for several chromones. Computational studies support the role of ALB as a bifunctional catalyst in this reaction and provide insights into the origin of the observed stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Sadhanendu Samanta, Jin Cui, Hidetoshi Noda, Takumi Watanabe, Masakatsu Shibasaki
Summary: A gram-scale syn-selective asymmetric vinylogous addition of butenolides to chromones, catalyzed by an Al-Li-BINOL (ALB) complex, was developed in this study. The diastereoselectivity reached 20:1 with 84-98% ee for various combinations of substrates. This protocol complements previous methods and improves selectivity for multiple chromones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Violet Yijang Chen, Ohyun Kwon
Summary: This paper presents a general synthetic protocol for polyalkyl furans using a Michael-Heck approach with sequential phosphine-palladium catalysis. The versatility of this method is demonstrated through the total syntheses of nine distinct polyalkylated furan natural products from readily available precursors.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Ying-Hong Huang, Zhan-Jiang Liu, Pei-Qiang Huang
Summary: This study describes the successful total synthesis of (+)-cylindricine D and its epi-isomer, as well as the synthesis of (+)-cylindricine C and E using a highly efficient method.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Analytical
Yujing Zuo, Zhiming Gou, Minggang Tian, Jingting Zhan, Weiying Lin
Summary: Rapid response is an important goal in fluorescence analysis technology, but it is often uncontrollable due to the limitations of the response mechanism and detection targets. In this study, a novel catalyst PNL-Br was synthesized and successfully incorporated into fluorescence analysis, showing a higher catalytic potential in thiol-Michael addition reactions. Notably, PNL-Br was an efficient catalyst for dithiothreitol (DTT) detection by fluorescence analysis, which was the first example of a catalysis system for fluorescent probe detection reactions.
SENSORS AND ACTUATORS B-CHEMICAL
(2023)
Article
Chemistry, Multidisciplinary
Kilian Colas, A. Catarina V. D. dos Santos, Stefanie Kohlhepp, Abraham Mendoza
Summary: The addition of organometallic reagents to aliphatic carboxylic acids for the synthesis of ketones is limited to organolithium reagents, but can be extended to Grignard reagents using a bulky aniline-derived turbo-Hauser base. This method allows for the straightforward preparation of a variety of aliphatic and perfluoroalkyl ketones.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Review
Biochemistry & Molecular Biology
Saba Munawar, Ameer Fawad Zahoor, Shafaqat Ali, Sadia Javed, Muhammad Irfan, Ali Irfan, Katarzyna Kotwica-Mojzych, Mariusz Mojzych
Summary: The Mitsunobu reaction is an important reaction in organic chemistry with wide synthetic applications. It can convert one functional group to another and change the stereochemical configuration of the products. It plays a significant role in the synthesis of natural products.
Article
Biochemistry & Molecular Biology
Kei Takenaka, Kensuke Kaneko, Nobuaki Takahashi, Shinichi Nishimura, Hideaki Kakeya
Summary: Unsaturated carbonyls are commonly found in bioactive small molecules and their non-specific reactions with biomolecules can lead to low efficacy and unexpected side effects of drugs. A new masking group, o-aminophenol, was discovered for ?,13-unsaturated ketones, which may be a promising tool for masking highly-reactive bioactive unsaturated carbonyl compounds.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
S. Erfan Masaeli, Mohsen Teimouri, Bhupendra Adhikari, Mahshid Attarroshan, James W. Akin, Selvam Raju, Sean L. Stokes, Joseph P. Emerson
Summary: We report a copper-catalyzed aza-Michael addition of aromatic amines with activated olefins using sodium trifluoroacetate (CF3CO2Na) as the mediator under mild, aqueous reaction conditions. This protocol is simple, employing a copper catalyst (10 mol%) and water as solvent. The reaction is compatible with aromatic amines containing both electron-donating (EDG) and electron-withdrawing (EWG) groups. Various substrates were tested, leading to good to moderate yields. (c) 2023 Elsevier Ltd. All rights reserved.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Organic
Yu Huang, Zhengqiang Liu, Wenbo H. Liu
Summary: This study demonstrates that a primary amine, when preactivated, can undergo nucleophilic addition to an aldehyde to form an alcohol. The key reagent for enabling this radical-polar crossover process is CrCl2. This reaction is highly selective for aldehydes and can tolerate numerous functional groups, which are typically incompatible with classical Grignard-type conditions. As a complementary approach to imine synthesis, this deaminative alcohol synthesis offers a broad expansion of chemical space accessible through aldehydes and amines.
Article
Chemistry, Multidisciplinary
Audrey Mauger, Maxime Jarret, Aurelien Tap, Remi Perrin, Regis Guillot, Cyrille Kouklovsky, Vincent Gandon, Guillaume Vincent
Summary: We synthesized highly strained pentacyclic caged framework of mavacuran alkaloids and successfully achieved the concise total synthesis of C-fluorocurine, C-profluorocurine, C-mavacurine, normavacurine, 16-epi-pleiocarpamine and taberdivarine H. A strategy involving late-stage Michael addition and intermolecular 1,4-addition reactions was designed. The first total syntheses of C-profluorocurine and C-fluorocurine were achieved through dihydroxylation of C-mavacurine and a pinacol rearrangement, respectively.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Medicine, Research & Experimental
Shi Wu, Yaobin Pang, Yingjie He, Xiaotong Zhang, Li Peng, Jing Guo, Jinhao Zeng
Summary: Atopic dermatitis (AD) presents a significant challenge for patients, and natural products such as puerarin, ferulic acid, and ginsenosides have shown promise in protecting against AD by inhibiting inflammatory cell activity. Future research should focus on developing natural products that address the clinical characteristics of AD for potential treatment options.
BIOMEDICINE & PHARMACOTHERAPY
(2021)
Article
Chemistry, Organic
Bin Mao, Zhi-Wei Chen, Jian-Fei Wang, Chao-Huan Zhang, Zhi-Qian Du, Chuan-Ming Yu
Summary: In this study, the enantioselective organocatalytic conjugate alkenylation of fi-substituted alkenyl benzimidazoles was achieved, leading to the formation of beta-stereogenic 2-alkyl benzimidazole derivatives with excellent enantio-selectivities. Chiral binaphthols were found to be effective catalysts for promoting the nucleophilic addition of bench-stable alkenyl trifluoroborate salts under mild conditions. By utilizing C=N-containing azaarenes as activating groups, the applications of these catalysts were expanded. The synthetic utility of this strategy was demonstrated by converting the products into several useful enantiomerically enriched benzimidazole building blocks.
Review
Pharmacology & Pharmacy
Qinfang Zheng, Ye Wang, Shuihan Zhang
Summary: This work reviews the progress in the phytochemical and biological investigations of bioactive components from Lobelia species, highlighting the shift in research focus towards novel chemical classes and molecular mechanisms of these components.
FRONTIERS IN PHARMACOLOGY
(2021)
