Article
Chemistry, Organic
Victoria Sinka, Daniel A. Cruz, Victor S. Martin, Juan I. Padron
Summary: The shortest enantioselective total syntheses of (+)-isolaurepinnacin and (+)-neoisoprelaurefucin were achieved using a common parallel synthetic strategy based on Prins-Peterson cyclization in their core construction. In only one step, a seven-membered ring oxacycle with the correct cis-stereochemistry ring closure and the Δ4 position of the endocyclic double bond in (+)-isolaurepinnacin was obtained. This unsaturation was also necessary to access the bromodioxabicycle in (+)-neoisoprelaurefucin.
Article
Chemistry, Multidisciplinary
Lada Dolejsova Sekerova, Zuzana Vavrikova, Thuy Trang Do, Eliska Vyskocilova, Libor Cerveny
Summary: Clarycet is an important fragrance used in various industrial applications. The optimal reaction conditions for its preparation were identified through two-step synthesis consisting of Prins cyclization and esterification. The experimental results demonstrated high yields of the desired product under specific reaction conditions.
RESEARCH ON CHEMICAL INTERMEDIATES
(2023)
Article
Biochemistry & Molecular Biology
Laura F. Pena, Enol Lopez, Angel Sanchez-Gonzalez, Asuncion Barbero
Summary: A convenient method has been developed for the regioselective synthesis of allyl- and vinylsilyl alcohols from a common precursor by selecting suitable reaction conditions. These alcohols have been used in silyl-Prins cyclizations to prepare disubstituted oxygenated heterocycles in a one-pot sequential reaction. The reaction outcomes are highly dependent on the starting alkenylsilyl alcohol and reaction conditions, with various competitive pathways observed. However, the use of vinylsilyl alcohols has shown promising results in the preparation of differentially substituted cis-2,6-dihydropyrans.
Article
Chemistry, Multidisciplinary
Efraim Reyes, Liher Prieto, Uxue Uria, Luisa Carrillo, Jose L. Vicario
Summary: The Prins reaction is a convenient method for synthesizing oxygen-containing heterocyclic compounds, especially tetrahydropyrans and tetrahydrofurans. Recent years have seen impressive improvements in its performance and scope, particularly in the development of new catalytic and enantioselective versions.
Article
Chemistry, Physical
Basile Lasne, Paivi Maki-Arvela, Atte Aho, Zuzana Vajglova, Kari Eranen, Narendra Kumar, Julian E. Sanchez-Velandia, Markus Peurla, Cecilia Mondelli, Javier Perez-Ramirez, Dmitry Yu Murzin
Summary: In this study, various heterogeneous micro- and mesoporous, acidic catalysts were examined for the selective synthesis of Florol (R). The results showed that a mildly acidic, microporous H-Beta-300 catalyst with a SiO2/Al2O3 ratio of 300 performed the best, achieving 72% selectivity and 99% conversion at 40 degrees C with a molar ratio of isoprenol to isovaleraldehyde of 1:5. More acidic zeolite catalysts exhibited slightly lower selectivity, while mesoporous catalysts with mild acidity and no strong Bronsted acid sites had the lowest selectivity.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Organic
Zhi-Bang Huang, Ming-Hao Zhao, Xu Liu, Lijia Wang
Summary: An indium catalyzed Prins/Friedel-Crafts tandem cyclization reaction has been developed, providing an efficient and practical method for the construction of various polycyclic indole frameworks with high diastereoselectivity and good functional group tolerance (30 examples, up to 98% yield with >95 : 5 dr). The resulting products are easily accessible for further chemical transformations.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Tarun Nallamilli, Anandarao Munakala, Rambabu Chegondi
Summary: In this study, a novel cascade annulation reaction of enone-tethered cyclohexadienones was achieved by using a combined Lewis acid catalyzed halogenation reaction and trimethylsilyl halide. This method provides a highly efficient way to synthesize bicyclic enones with multiple stereocenters.
Article
Chemistry, Physical
Eva Vrbkova, Tomas Prejza, Miloslav Lhotka, Eliska Vyskocilova, Libor Cerveny
Summary: The Prins intramolecular cyclization of citronellal to produce isopulegol was studied using modified zeolites BETA with different Si/Al ratios and metal loadings of iron or zinc. It was found that impregnation with metal on Beta materials with Si/Al ratios of 38 and 75 increased catalytic activity, along with an increase in weak acid sites. In particular, Beta 38 with 1 wt.% iron loading showed high citronellal conversion and selectivity for isopulegol formation.
Article
Chemistry, Physical
Augusto L. P. de Meireles, Kelly A. da Silva Rocha, Elena F. Kozhevnikova, Ivan V. Kozhevnikov, Elena V. Gusevskaya
Summary: The H3PW12O40 heteropoly acid supported on SiO2 as a catalyst and its bulk acidic cesium salt Cs2.5H0.5PW12O40 have been demonstrated to be highly active and recyclable for the Prins cyclization reaction, leading to the efficient synthesis of the valuable floral odorant Florol? from isoprenol and isovaleraldehyde. The use of dimethylcarbonate or diethylcarbonate as green reaction media, along with low catalyst loadings and moderate conditions, contribute to the sustainability of the method.
MOLECULAR CATALYSIS
(2021)
Review
Chemistry, Organic
Asha Budakoti, Pradip Kumar Mondal, Prachi Verma, Jagadish Khamrai
Summary: The Prins reaction is an important technique for the synthesis of tetrahydropyran skeletons with various substituents, and has been successfully applied in the total synthesis of bioactive macrocycles and related natural products.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Vallabhareddy Satteyyanaidu, Rapelli Chandrashekhar, B. V. Subba Reddy, Claudia Lalli
Summary: This study proposes the synthesis of biologically relevant hexahydro-1H-pyrano[3,4-c]chromenes through a tandem Prins/Friedels-Crafts process catalyzed by BF3.Et2O. The diastereoselectivity of the process is controlled by the geometry of the homoallylic alcohol. Additionally, high yields and good diastereoselectivity of the Prins product can be achieved when the reaction is promoted by AlCl3 as Lewis acid in the presence of an external nucleophile.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Debobrata Paul, Subhendu Das, Sanu Saha, Himangshu Sharma, Rajib Kumar Goswami
Summary: The intramolecular Heck reaction plays a significant role in synthesizing natural products by constructing various cyclic scaffolds. It serves as a strategic step in the synthesis of different natural products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Marvin Fresia, Thomas Lindel
Summary: The synthesis of ABCD tetracyclic partial structures of fungal indole diterpenes janthitrem B, JBIR-137, and shearinine G is reported, starting from 5-formylated indoline coupled to a dihydropyran moiety via Prins cyclization. The hydroxylated tetracyclic western half of janthitrem B was obtained in eight steps with a 10% overall yield. Alternative approaches using alkynylated precursors, including gold-catalyzed cycloisomerization, were also discussed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Sa Guo, Xin Wang, Dongyang Zhao, Zhiguo Zhang, Guisheng Zhang, Shi Tang, Kai Sun
Summary: In this study, we present a sequential radical alkoxycarbonylation/cyclization/hydrolysis reaction using carbazates as eco-friendly ester sources. Various structurally diverse ester-substituted quinolinones were obtained in moderate to high yields. The easy scale-up operation and potential for product derivatization make this method attractive for the synthesis of other valuable ester-containing N-heterocycles.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Sudip Shit, Surjya Kumar Bora, Archana Kumari Sahu, Anil K. Saikia
Summary: This study demonstrates the synthesis of spiro[furan-2,1'-isoindolin]-3'-ones from 2-(4-hydroxybut-1-yn-1-yl)benzonitriles and aryl aldehydes. The reaction involves the formation of dihydrofuranylideneisoindolinone through intramolecular Prins and Ritter reactions, followed by ring opening and cyclization to produce the spiro-cyclic compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
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.