Article
Chemistry, Applied
Tsai-Hui Lung, Yi-Ru Chen, Chen-Ling Chang, Wey-Chyng Jeng, Pei-Shan Wu, Sandip Sambhaji Vagh, Gangababu Marri, Yi-Fang Lin, Wenwei Lin
Summary: A catalyst-controlled diversity-oriented synthesis of spirohydroquinoline-indandiones and 3-methylenehydroquinoline-indandiones was reported using ortho-sulfonamidophenyl-substituted para-quinone methides and allylidene-indandiones. Organobases such as DMAP or TMG were utilized to selectively control the reaction pathway, resulting in products with yields of 40-99% and excellent diastereoselectivities. Mechanistic studies revealed that spirohydroquinoline-indandione was the kinetic product, which underwent an unusual base-initiated 1,3-nitrogen rearrangement process to afford 3-methylenehydroquinoline-indandione in the presence of TMG.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Jie Liu, Gregor S. Cremosnik, Felix Otte, Axel Pahl, Sonja Sievers, Carsten Strohmann, Herbert Waldmann
Summary: This study presents the design and synthesis of a collection of 155 pyrroquinoline pseudo-NPs, combining fragments characteristic of tetrahydroquinoline and pyrrolidine classes in novel arrangements. Cheminformatic analysis and biological evaluation revealed chemically diverse pseudo-NP classes with distinct bioactivity patterns, dependent on fragment connectivity and regioisomeric arrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Giorgia Vinciarelli, Giuseppe Barreca, Marianna Coppola, Silvano Ronzoni, Maurizio Taddei
Summary: Ethyl diazoacetate (EDA) reacts with alkynes in a water micelle environment to form pyrazoles. The reaction outcome depends on the pH, with different substituted positions obtained under different pH conditions. The presence of a surfactant is crucial for obtaining high yields and clean products. The same method is applicable for the synthesis of substituted pyrazolines.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Soojun Park, Jiwoo Lee, Jae Hyun Kim, Yeji Jeong, Seokwoo Lee, Su Won Lee, Sanghee Kim
Summary: A concise total synthesis of salinosporamides and cinnabaramides was achieved through the combined use of memory of chirality and dynamic kinetic resolution principles, involving aldol reactions and hydrolysis reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Kevin Rafael Sokol, Thomas Magauer
Summary: This review provides an overview of synthetic methods and strategies for constructing oxepin and dihydrooxepin motifs in the context of natural product synthesis, highlighting key steps of each example.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Brandon C. Derstine, Alina J. Cook, James D. Collings, Joseph Gair, Josep Sauri, Eugene E. Kwan, Noah Z. Burns
Summary: In this study, we report the first total synthesis and full stereochemical assignment of (+)-discorhabdin V. The synthesis was achieved through a highly convergent strategy enabled by scalable access to the two key components. Our work lays the foundation for future biological evaluation of nitrogen-bridged discorhabdins.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Argha Saha, Chiranjit Sen, Srimanta Guin, Chandan Das, Debajit Maiti, Subhabrata Sen, Debabrata Maiti
Summary: We have developed a photoinduced protocol for the synthesis of pharmaceutically important oxazole molecules using diazo- and nitrile-containing reactants. The process involves the initial photolysis of the diazo compound to afford singlet carbenes, which are tapped by nitriles in a [3+2] cycloaddition fashion to give substituted oxazoles. The protocol is applicable for the synthesis of diverse oxazoles and can be used for drug synthesis and isotope labeling.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Joseph Benford-Ward, Sanaz Ahmadipour, Aliya Sembayeva, Louise Male, Richard S. Grainger
Summary: The synthesis of the naturally occurring (+)-dictyoxetane was achieved through catalytic asymmetric synthesis and the use of alternative methods. The study also investigated a range of related reactions to the synthesis target.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Review
Chemistry, Inorganic & Nuclear
Vladimir B. Kharitonov, Dmitry V. V. Muratov, Dmitry A. Loginov
Summary: This review comprehensively summarizes the use of cyclopentadienyl complexes of Group 9 metals in the total synthesis of natural compounds, including catalyzing cycloaddition, transfer hydrogenation, and C-H activation reactions.
COORDINATION CHEMISTRY REVIEWS
(2022)
Article
Chemistry, Organic
Yang Feng, Bo Chang, Yuanyuan Ren, Fangxia Zhao, Ke-Hu Wang, Junjiao Wang, Danfeng Huang, Xiaobo Lv, Yulai Hu
Summary: An efficient and practical method for the synthesis of trifluoromethylpyrrolopyrazole derivatives was developed by utilizing readily available trifluoromethyl building blocks in a [3+2] cycloaddition reaction. The reaction proceeds smoothly under mild conditions, providing good to excellent yields of 3-trifluoromethylated pyrrolidino[3,4-c]pyrazolidin-4,6-dione and 3-trifluoromethylated dihydropyrrolo[3,4-c]pyrazole-4,6(1H,5H)-diones. The latter can be further oxidized to 3-trifluoromethylated pyrrolo[3,4-c]pyrazole-4,6(1H,5H)-diones using TCCA.
Article
Chemistry, Organic
Shunya Hara, Shigekazu Ito
Summary: The catalytic intermolecular [2+2] cycloaddition of electron-rich alkynes and trifluoroiminopyruvate was demonstrated, affording the corresponding CF3-substituted isolable 2-azetines. Using titanium(IV) tetrachloride as a catalyst effectively promoted the desired [2+2] cycloaddition, providing 2-azetines. The regioselectivity was complete with electron-rich aryl-substituted inner alkynes, and a silyl group was effective for inducing the dominant [2+2] cycloaddition pathway, leading to the formation of a 6-membered cyclic sulfonamide.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Dibya Das, Ashis Kumar Jena, Chandan Kumar Pal, Laurens Bourda, Kristof Van Hecke
Summary: A mild, efficient, and stable copper iodide nanoparticle (CuI NP)-catalyzed method has been developed for the regioselective synthesis of 3-nitro-2-arylimidazo[1,2-a]pyridines. The method provides good to excellent yields of the desired products and the nanocatalyst showed good reusability up to three consecutive cycles. The use of molecular oxygen as an oxidant is advantageous from an economic and environmental standpoint.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Mengmeng Xu, Min Hou, Haibing He, Shuanhu Gao
Summary: This study developed a new synthetic method for constructing aryltetralin lactone lignans and successfully synthesized several natural lignans using this methodology. The synthesized aglacins and small-molecule library created new opportunities for SAR studies of the podophyllotoxin family of natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jacob S. Bestwick, David J. Jones, Helen E. Jones, Panagiotis G. Kalomenopoulos, Rafal Szabla, Andrew L. Lawrence
Summary: A biomimetic synthetic strategy was used to synthesize (+/-)-ulodione A and predict two potential natural products. Computational investigations into biosynthetic selectivity guided the chemical synthesis. This work demonstrates the importance of biosynthetic considerations in guiding efficient synthetic strategies and anticipating new natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Lixin Liang, Lian-Dong Guo, Rongbiao Tong
Summary: The six-membered heterocycles containing oxygen and nitrogen are commonly found in bioactive molecules and the chemical synthesis of fully functionalized pyrans and piperidines has attracted interest from synthetic chemists. The Achmatowicz rearrangement represents a unique strategy using biomass-derived furfuryl alcohols as starting materials, providing opportunities for addressing synthetic challenges. This Account summarizes the work done on exploiting AchR to address challenges in various organic synthesis, focusing on green chemistry, organic methodology, and total synthesis of natural products.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
