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, Organic
Xiao-Ping Liang, Min Luo, Li Kang, Long-Xing Tang, Qing Liang, Yuan-Lin Liu, Zi Yang, Chun-Tao Zhang, Cai-Yun Peng, Rong-Geng Fu
Summary: A novel and facile metal-free method for the green synthesis of 2-amino-4-arylthiazole derivatives through a three-component cascade reaction is reported. The reaction involves aromatic methyl ketones, elemental sulfur, and cyanamide, and forms one C-N bond and two C-S bonds in one-pot protocol without using catalysts.
TETRAHEDRON LETTERS
(2022)
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, Applied
Sara Zahim, Kenny Delacroix, Agathe Carlier, Thierry Berranger, Julie Bergraser, Pierre-Georges Echeverria, Laurent Petit
Summary: This study describes the recent efforts to find an efficient and scalable route to tetrahydro-4H-pyran-4-one using commercially available starting materials. The work culminated in the preparation of over 20 kg of the title compound in the pilot plant facility.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
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, Organic
Jonathan Trevorrow, Anne O'Kearney-McMullan, Lucie Miller Potucka, Adrian P. Dobbs
Summary: In this study, we report a novel and highly efficient method for the synthesis of hydroxydi- and hydroxytetra-hydropyrans as spiroketal precursors. This method bypasses the challenges associated with traditional multistep syntheses and protecting group manipulation, providing a new pathway for studying the spiroketal moiety.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Zhen-Zhen Chen, Dong-Zhao Yang, Ying-Ying Dong, Mei Chi, Shou-Zhi Pu, Qi Sun
Summary: Hafnium(IV) triflate (Hf(OTf)(4)) has been identified as a potent catalyst for the direct three-component synthesis of beta-carbamate ketones. This new method, featuring a low catalyst loading, fast reaction rate, and solvent-free conditions, provides easy access to a variety of carbamate-protected Mannich bases. Mechanistic investigation reveals that the three-component reaction proceeds through sequential aldol condensation and aza-Michael addition, rather than the Mannich-type pathway.
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
E. Pravardhan Reddy, P. Padmaja, P. Chandra Shekar, K. Kamalaker Reddy, B. V. Subba Reddy
Summary: An efficient synthesis of 2-aryl-4-chloro-tetrahydropyrans has been achieved using FeCl3 as a promoter through a sequential oxidation/Prins cyclization, with benzyl chlorides and homoallylic alcohols as substrates, resulting in high yields. It is noteworthy that this is the first report on the use of benzyl chlorides as surrogates for aldehydes in the Prins cyclization.
TETRAHEDRON LETTERS
(2022)
Article
Multidisciplinary Sciences
Shuai Shi, Wenting Qiu, Pannan Miao, Ruining Li, Xianfeng Lin, Zhankui Sun
Summary: The authors expanded the scope of the classical Mannich reaction to enolizable aldehydes by employing a radical process, resulting in a streamlined synthesis of gamma -amino-carbonyl compounds.
NATURE COMMUNICATIONS
(2021)
Article
Biochemistry & Molecular Biology
Max Van Hoof, Santhini Pulikkal Veettil, Wim Dehaen
Summary: This study presents a practical method for the synthesis of 4-sulfonyl-1,5-disubstituted-1,2,3-triazoles through a room-temperature, aerobic copper-catalyzed three-component reaction of aromatic ketones, sodium sulfinates, and azides. The procedure provides a facile access to the target compounds in yields ranging from 34% to 89%, offering an efficient synthetic pathway for these structures.
Article
Chemistry, Applied
Lingfeng Wang, Song Li, Xuqiong Xiao, Weiming Xu, Pengfei Zhang, Yongmin Ma
Summary: A three-component domino approach for the synthesis of chroman-spiroquinazolin(thi)ones is described, which involves a condensation reaction followed by a hetero-Diels-Alder annulation. The reaction shows broad substrate scope and can be conducted under metal-free catalytic conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Shuyu Meng, Wentao Guo, Jie Liu, Jie Zheng, Quanrui Wang
Summary: A tandem Prins/Friedel-Crafts cascade strategy has been developed for the synthesis of hexahydro-2H-benzo[g]chromene derivatives. This method enables the formation of three new chemical bonds in one single operation with high yields and stereoselectivity in most cases. Moreover, a variety of spiro derivatives could also be synthesized successfully, further proving the robustness of this methodology.
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, Multidisciplinary
Eva Vrbkova, Lada Sekerova, Eliska Vyskocilova, Martin Zapletal, Libor Cerveny
Summary: Several types of modified zeolite BETA38 with different iron loading were prepared and characterized. The introduction of iron significantly enhanced the catalytic activity of the materials, regardless of the amount of iron loading. The material with 1wt% Fe loading exhibited high conversion rates in various reactions. Particularly, the Fe loaded Beta 38 showed a significant catalytic effect in the Prins reaction of benzaldehyde with isoprenol.
RESEARCH ON CHEMICAL INTERMEDIATES
(2022)
Article
Chemistry, Organic
Hari P. R. Mangunuru, Jayasudhan R. Yerabolu, Dong Liu, Guijun Wang
TETRAHEDRON LETTERS
(2015)
Article
Chemistry, Organic
Had P. R. Mangunuru, Jayasudhan Reddy Yerabolu, Guijun Wang
TETRAHEDRON LETTERS
(2015)
Article
Chemistry, Organic
Gavin B. Rice, Jayasudhan R. Yerabolu, Ramanarayanan Krishnamurthy, Greg Springsteen
Article
Chemistry, Multidisciplinary
Guijun Wang, Anji Chen, Hari P. R. Mangunuru, Jayasudhan Reddy Yerabolu
Article
Multidisciplinary Sciences
Greg Springsteen, Jayasudhan Reddy Yerabolu, Julia Nelson, Chandler Joel Rhea, Ramanarayanan Krishnamurthy
NATURE COMMUNICATIONS
(2018)
Article
Chemistry, Multidisciplinary
B. V. Subba Reddy, P. Sivaramakrishna Reddy, Y. Jayasudhan Reddy, N. Bhaskar, B. Chandra Obula Reddy
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
(2013)
Article
Chemistry, Organic
Jhillu S. Yadav, Poli Adi Narayana Reddy, Yerabolu Jayasudhan Reddy, Syeda Meraj, Attaluri R. Prasad
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Organic
J. S. Yadav, Y. Jayasudhan Reddy, P. Adi Narayana Reddy, B. V. Subba Reddy
Article
Chemistry, Organic
B. V. Subba Reddy, Supriya Ghanty, N. Siva Senkar Reddy, Y. Jayasudhan Reddy, J. S. Yadav
SYNTHETIC COMMUNICATIONS
(2014)
Article
Chemistry, Organic
B. V. Subba Reddy, B. Phaneendra Reddy, P. Sivaramakrishna Reddy, Y. Jayasudhan Reddy, J. S. Yadav
TETRAHEDRON LETTERS
(2013)
Article
Multidisciplinary Sciences
Zaigham M. Khan, Alexander M. Real, William M. Marsiglia, Arthur Chow, Mary E. Duffy, Jayasudhan R. Yerabolu, Alex P. Scopton, Arvin C. Dar
Article
Chemistry, Multidisciplinary
Brooke A. Anderson, Kevin Fauche, Suneesh C. Karunakaran, Jayasudhan R. Yerabolu, Nicholas V. Hud, Ramanarayanan Krishnamurthy
Summary: The study reveals that cyanuric acid destabilizes supramolecular assemblies in RNA containing CA and CA-ribose nucleoside, contrary to previous reports. This suggests the existence of new paradigms for reorganizing nucleic acid structures.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Mahipal Yadav, Sunil Pulletikurti, Jayasudhan R. Yerabolu, Ramanarayanan Krishnamurthy
Summary: The study reveals that cyanide acts as a mild and efficient reducing agent in mediating abiotic transformations of tricarboxylic acid intermediates and derivatives. The results suggest the existence of a simpler prebiotic metabolic pathway, bypassing the challenging reductive carboxylation steps.
Meeting Abstract
Biochemistry & Molecular Biology
Arthur Chow, Jayasudhan R. Yerabolu, Kyna Reyes, Alex Scopton, Arvin C. Dar
Article
Chemistry, Multidisciplinary
Jayasudhan Reddy Yerabolu, Charles L. Liotta, Ramanarayanan Krishnamurthy
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
