Review
Chemistry, Organic
Paula Franova, Stefan Marchalin
Summary: This review presents the latest developments in the synthesis of naturally occurring polyhydroxylated indolizidines and their synthetic enantiomers. Several novel polyhydroxylated indolizidines with inhibitory activity are reported.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Debasmita Mondal, Subhendu Pramanik, Chinmay Chowdhury
Summary: Palladium-catalyzed reactions provide an easy access to desired compounds, and the choice of suitable phosphine ligands is crucial for the success of the reaction.
Article
Chemistry, Multidisciplinary
Shicheng Shi, Farbod Salahi, Hunter B. Vibbert, Maleeha Rahman, Scott A. Snyder, Jack R. Norton
Summary: In this reaction, alpha-vinyl borates are converted into alpha-boryl radicals under H-2 in the presence of a cobaloxime catalyst, leading to densely functionalized heterocycles with tertiary substituents on Bpin. The reaction exhibits good functional group tolerance and wide scope, with the resulting boronate products being convertible into other useful functionalities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Hui-Xin Xiao, Pan-Pan Li, Bin Pan, Wu Liang, Fei Du, Yu Yu
Summary: A new alkoxycarbonylation/cyclization reaction of unactivated alkenes containing heterocycles is reported. Silver carbonate is employed as the catalyst under photoirradiation. The method provides efficient access to valuable pharmaceutical compounds and natural product analogues containing quinazolinone-fused esters.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jiawei Sun, Yuan Chen, Sherif Shaban Ragab, Wei Gu, Ziqiang Tang, Yuexun Tang, Wenjun Tang
Summary: In this study, an unsaturation-functionalization strategy was applied to address the C19-hydroxylation issue for efficient synthesis of polyhydroxylated steroids. The synthetic method featured an effective asymmetric dearomative cyclization and various reactions to introduce the polyhydroxy functionalities. Ultimately, the total synthesis of 19-hydroxysarmentogenin and ouabagenin was achieved, demonstrating the synthetic versatility and practicality of these polyhydroxylated steroids in the search for new therapeutic agents.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Matteo Faltracco, Said Ortega-Rosales, Elwin Janssen, Razvan C. Cioc, Christophe M. L. Vande Velde, Eelco Ruijter
Summary: The unexpected discovery in a seemingly trivial reaction led to the selective formation of a new carbazole product. This reaction, by carefully varying substituents, revealed a complex cascade mechanism with at least 10 elementary steps that could be directed towards different carbazole derivatives.
Article
Chemistry, Organic
Shi-Yi Zhuang, Yong-Xing Tang, Jin-Yi Liu, Xiang-Long Chen, Jin-Tian Ma, Yan-Dong Wu, Kai-Lu Zheng, An-Xin Wu
Summary: In this study, an I2-DMSO-mediated cascade reaction using commercially available substrates, methyl ketones and 1,2,3,4-tetrahydroisoquinolines (THIQs), has been developed for the synthesis of pyrrolo[2,1-a]isoquinoline derivatives. The metal-free process involves the N-H/alpha-C(sp3)-H difunctionalization of THIQ, leading to the formation of two C-C bonds and one C-N bond in one pot under mild conditions. Additionally, a quaternary carbon center is efficiently constructed in this transformation.
Article
Chemistry, Multidisciplinary
You-lu Pan, Xiao-meng Gong, Rong-rong Hao, Shen-xin Zeng, Zheng-rong Shen, Wen-hai Huang
Summary: A facile CuBr2 induced radical relay addition/cyclization reaction has been developed for the synthesis of a broad range of sulfonated compounds. Some of the synthesized compounds exhibited bioactivity against cancer cell lines. This protocol offers advantages of low-cost, base-free, simple operation, and broad functional group tolerance.
Article
Chemistry, Multidisciplinary
Kaixia Sui, Yuting Leng, Yangjie Wu
Summary: A highly efficient method for synthesizing difluoroarymethyl-substituted benzimidazo[2,1-a]isoquinolin-6(5H)-ones was developed using 2-arylbenzoimidazoles with alpha,alpha-difluorophenylacetic acid as reaction substrates through radical cascade cyclization. The strategy offers excellent functional group tolerance and enables the generation of the desired products in good yields under base- and metal-free conditions.
Article
Plant Sciences
Quynh N. Quach, Keith Clay, Stephen T. Lee, Dale R. Gardner, Daniel Cook
Summary: This study reports the occurrence of heritable fungal endosymbiosis in the Convolvulaceae family and investigates the bioactive metabolites produced by the symbiotic fungi. The results show that approximately 40% of morning glory species have associations with two distinct fungi that produce ergot alkaloids, indole diterpene alkaloids, and swainsonine. The symbiotic relationships occur in different phylogenetic clades, and host species have larger seed size compared to nonsymbiotic species.
Article
Chemistry, Organic
Hong Qiu, Lingfeng Tong, Zhongren Lin, Zheyao Li, Haosong Ren, Teng Wang, Xinhong Yu
Summary: This study reports a one-pot three-component reaction based on an oxidative dearomatization strategy to synthesize 5-hydroxyindole derivatives via a ZnI2-catalyzed tandem process. The multi-unit reactions for the construction of a new C-C bond and two C-N bonds are simple and efficient under mild conditions, and the yield of the target product is as high as 91%.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Dan Xiao, Xin Zhao, Jiang Lei, Mengqian Zhu, Liang Xu
Summary: A new synthesis method has been developed to form the bridged [6-6-6] ABE tricyclic ring analogues of methyllycaconitine with C-1 oxygenated substituents, using efficient aza-annulation of beta-enamino ketone followed by a facile decarboxylation to form BE rings. Subsequent elaboration to form the A ring was achieved by a transannular acyl radical cyclization with concomitant equipment of the key C-1 oxygen functionality.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Yanyu Chen, Zhengyuan Xin, Hui Wang, Haibing He, Shuanhu Gao
Summary: Zoanthamine alkaloids are structurally unique and complex natural products that have a broad range of biological activities and potential in drug discovery. The synthesis of norzoanthamine and the core structure of zoanthenol have been studied, focusing on the construction of challenging adjacent stereocenters using radical reactions as key steps. The research provides insights into the biological profile of norzoanthamine and expands the understanding of zoanthamine alkaloids.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Xin Wang, Jinhuan Dong, Xianxiu Xu, Bo Tang
Summary: A base-catalyzed double annulation methodology has been developed for the efficient synthesis of 4-azafluorene and 4-azafluorenone derivatives. In contrast to traditional 1,3-dipolar reactions, the active methylene and isocyano groups of isocyanoacetate function as nucleophiles in this domino transformation.
Article
Chemistry, Organic
Carlos Lazaro-Milla, Hikaru Yanai, Pedro Almendros
Summary: A new sequential cyclization cascade method has been successfully developed in this study for the efficient preparation of functionalized tricyclic indoline cores bearing two contiguous stereocenters.
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
