Article
Biochemistry & Molecular Biology
Younggyu Kong, Pulla Reddy Boggu, Gi Min Park, Yeon Su Kim, Seong Hwan An, In Su Kim, Young Hoon Jung
Summary: The total synthesis of eliglustat, an approved drug for non-neurological Gaucher disease, starting from 1,4-benzodioxan-6-carbaldehyde is described. The synthesis involves Sharpless asymmetric dihydroxylation and diastereoselective amination steps, with chlorosulfonyl isocyanate as a key reactant.
Article
Chemistry, Multidisciplinary
Xiaoping Yue, Yitong Li, Minjie Liu, Di Sang, Zedu Huang, Fener Chen
Summary: The first systematic study of ketoreductase-catalyzed dynamic reductive kinetic resolution on aryl alpha-chloro beta-keto esters was conducted. The study successfully synthesized diverse chiral anti-aryl alpha-chloro beta-hydroxy esters and achieved a record-breaking space-time yield of the key intermediate of diltiazem. Furthermore, an eight-step synthesis of diltiazem, clentiazem, and siratiazem was accomplished using this versatile biocatalytic reduction reaction.
CHEMICAL COMMUNICATIONS
(2022)
Article
Multidisciplinary Sciences
Bing Zhang, Chuntian Qiu, Shan Wang, Hua Gao, Kunyi Yu, Zhaofei Zhang, Xiang Ling, Wei Ou, Chenliang Su
Summary: The controllable electrocatalytic deuteration of halides using heavy water as a D-source presents a promising method for the preparation of valuable D-labelled chemicals and pharmaceuticals, with high efficiency and selectivity. This electrochemical method can be tuned by adjusting the applied voltages to control the reaction efficiency and selectivity, showing great potential for producing value-added fine chemicals.
Review
Biochemistry & Molecular Biology
Aqsa Mushtaq, Ameer Fawad Zahoor, Muhammad Bilal, Syed Makhdoom Hussain, Muhammad Irfan, Rabia Akhtar, Ali Irfan, Katarzyna Kotwica-Mojzych, Mariusz Mojzych
Summary: Sharpless asymmetric dihydroxylation is an important reaction in enantioselective synthesis of chiral vicinal diols. It involves the treatment of alkene with osmium tetroxide and optically active quinine ligand. This review highlights the significance of Sharpless asymmetric dihydroxylation in the total synthesis of various natural products since 2020.
Article
Chemistry, Multidisciplinary
Amanpreet Kaur, Anju Gehlawat, Ranjana Prakash, Satyendra Kumar Pandey
Summary: The efficient enantioselective approach described in the synthesis of Sacubitril 1, a NEP inhibitor used in combination with Valsartan for heart failure treatment, involves Evan's asymmetric alkylation, Sharpless asymmetric dihydroxylation (AD) and Heck coupling reactions as key steps.
Article
Plant Sciences
Ashvin J. Gangani, Praveen Kumar, Rodney A. Fernandes
Summary: By synthesizing from the chiral pool material D-gluconob-delta-lactone, the two types of lactones can be obtained through a few steps of reactions, with one operation yielding syn-lactones and another operation yielding anti-lactones in high yields.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Chemistry, Multidisciplinary
Marta Pytlarczyk, Jakub Herman, Michal Czerwinski, Yuki Arakawa, Hideto Tsuji, Przemyslaw Kula
Summary: This paper introduces a method for synthesizing deuterated liquid crystals using a continuous flow system, and demonstrates through experiments and theoretical calculations that deuterium-labeled liquid crystals exhibit increased photochemical stability. The physical and chemical properties of deuterated and non-labeled liquid crystals are also compared.
Review
Chemistry, Multidisciplinary
Krishnaji Tadiparthi
Summary: This review discusses the synthetic approaches of chiral and racemic forms of centrolobines from 2002 to date, highlighting the importance of construction of tetrahydropyran unit and generation of chirality in the synthesis process. It systematically presents various methods developed by different research groups in the total syntheses of centrolobines.
Article
Chemistry, Organic
Ravikrishna Dada, Srinivasarao Yaragorla
Summary: Herein, we describe a stereoselective total synthesis of phomonol, a natural product, starting from readily available D-aspartic acid. The key steps involve Wittig olefination, Sharpless asymmetric dihydroxylation, Grignard addition, diastereoselective reductive etherification, and Wacker oxidation.
SYNTHETIC COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Ravi Gurram, Srihari Pabbaraja
Summary: A stereoselective synthetic strategy for (+)-paecilomycin F was developed using readily available 2,4,6-trihydroxy benzoic acid and chiral R(+)-propylene oxide. The synthesis involved key reactions such as regioselective Grignard reaction, Wittig reaction, Sharpless asymmetric dihydroxylation, Barbier-type allylation, Stille-coupling, and ring-closing metathesis. The target molecule was successfully synthesized in a 7-step linear sequence with a 20% overall yield starting from 2,4,6-trihydroxy benzoic acid, or a 12-step sequence with a 12.95% overall yield starting from R(+)-propylene oxide.
LETTERS IN ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Potham Rajendar, Srinivasa Desikan, Gattu Sridhar, Bharat Kumar Tripuramallu
Summary: An enantioselective total synthesis of a novel gingerol-related compound 4-((3S,5R)-3,5-dihydroxynonadecyl)phenol, isolated from Chilean desert plants, has been achieved using a concise ten-step sequence starting from a commercially available 4-(but-3-enyl) phenol. Sharpless asymmetric dihydroxylation, Grignard reaction and Iodine-induced electrophilic cyclization were used as key steps.
SYNTHETIC COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Namdeo Gangathade, Kiranmai Nayani, Hemalatha Bukya, Prathama S. Mainkar, Srivari Chandrasekhar
Summary: A scalable synthesis of L-allo-enduracididine is achieved from commercially available (S)-glycidol in ten linear steps, involving well-established synthetic transformations. The synthetic route is flexible and can synthesize all four diastereomers by changing the stereochemistry of glycidol and Sharpless asymmetric dihydroxylation reagent.
Article
Chemistry, Multidisciplinary
Deyu Liu, Yusheng Lei, Xiaozhou Ji, Yilei Wu, Yangju Lin, Yunfei Wang, Song Zhang, Yu Zheng, Yuelang Chen, Jian-Cheng Lai, Donglai Zhong, Hao-Wen Cheng, Jerika A. Chiong, Xiaodan Gu, Sangah Gam, Youngjun Yun, Jeffrey B-H Tok, Zhenan Bao
Summary: This study improves the understanding of the design concept by investigating the effect of bulky side groups asymmetrically substituted on conjugated polymer semiconductor backbones. The results show that the introduction of conjugated rigid fused-rings with bulky side groups can improve the mechanical stretchability and electrical properties of the material.
ADVANCED FUNCTIONAL MATERIALS
(2022)
Article
Chemistry, Organic
Weiwei Wang, Yihao Li, Xinlei Liu, Yu Zhao, Mingan Wang
Summary: A series of novel compounds were designed and synthesized with certain fungicidal activities against various fungi. The compounds showed potential for optimization to improve their fungicidal activity, with some compounds exhibiting EC50 values in the range of 20.5-40.6 μg/mL against specific fungi in vitro and in vivo.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Correction
Polymer Science
Madison Mooney, Audithya Nyayachavadi, Angela Awada, Ekaterini Iakovidis, Yunfei Wang, Mei-Nung Chen, Yuzi Liu, Jie Xu, Yu-Cheng Chiu, Xiaodan Gu, Simon Rondeau-Gagne
Summary: This article investigates the application of asymmetric side-chain engineering in semiconducting polymers, providing a new platform for greener processing and post-functionalization of organic electronics.
Article
Chemistry, Organic
Chada Raji Reddy, Ketan Wadekar, Karna Nair, Y. Lakshmi Prapurna
Summary: A new approach for synthesizing benzofurans from non-aromatic precursors is reported. The method involves sequential DBU-mediated cycloisomerization for furanylation followed by benzene ring construction via oxidative aromatization. The reaction has advantages such as atom- and pot-economy, simple reaction conditions, easy preparation of starting materials, and access to diverse substituted benzofurans.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Chada Raji Reddy, Siddique Z. Mohammed, Paridala Kumaraswamy, Roshan Chandrakant Kajare, Amol D. Patil, V. S. Rao Ganga, Andhavaram Ramaraju, Balasubramanian Sridhar
Summary: An effective synthetic approach for the construction of diverse bicyclic fused cyclopentenones from Morita-Baylis-Hillman (MBH) carbonates of propiolaldehydes has been demonstrated. The transformation involves the propargylation of an alkenylamine with an MBH carbonate followed by the Pauson-Khand reaction to yield cyclopentenone fused with aza-cycles having additional functionality.
SYNTHESIS-STUTTGART
(2022)
Article
Biochemistry & Molecular Biology
Nicolas Levoin, Appala Venkata Ramana Murthy, Vennu Narendar, Nangunoori Sampath Kumar, Pasula Aparna, Anagani Kanaka Durga Bhavani, Chada Raji Reddy, Paul Mosset, Rene Gree
Summary: A series of compounds with piperidine-triazole scaffolds were found to have strong affinity for dopamine and sigma receptors, with selectivity towards specific receptors and channels. The lead compound showed agonist activity and suggested the presence of a calcium-binding regulatory site.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Chada Raji Reddy, Veeramalla Ganesh, Nagender Punna
Summary: Unprecedented domino aza-annulations of (E)-2-en-4-ynyl-acetonitriles with sodium azide under metal-and oxidant-free conditions for the assembly of triazolo-pyridines are accomplished. The developed strategy offers broad substrate scope and demonstrated its synthetic utility via denitrogenative coupling of fused triazoles with different nucleophiles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Dabbugoddu Brahmaiah, Anagani Kanaka Durga Bhavani, Pasula Aparna, Nangunoori Sampath Kumar, Helene Solhi, Remy Le Guevel, Blandine Baratte, Thomas Robert, Sandrine Ruchaud, Stephane Bach, Surender Singh Jadav, Chada Raji Reddy, Paul Mosset, Nicolas Gouault, Nicolas Levoin, Rene Gree
Summary: Three series of CLK1 inhibitors were designed, synthesized, and tested against CLKs and DYRK1A kinases. A promising derivative 12g was discovered, showing significant inhibition activity against HsCLK1 and HsDYRK1A. Molecular modeling and kinome scan analysis further supported these results, suggesting the potential for developing selective inhibitors in this kinase family.
Article
Chemistry, Multidisciplinary
Chada Raji Reddy, Muppidi Subbarao, Dattahari H. Kolgave, Uprety Ajaykumar, Puthiya Purayil Vinaya
Summary: An efficient and straightforward method for the synthesis of diversified seleno-azaspiro-2,5-cyclohexadienones from N-(4-methoxy aryl)propiolamides using elemental selenium and boronic acids has been demonstrated. This method can also be extended to N-(4-methoxy aryl)propiolates and biaryl ynones to access the corresponding selenylated oxospiro-2,5-cyclohexadienones and spiro[5,5]trienones, respectively.
Article
Chemistry, Multidisciplinary
Jadhav Rahul Dhanaji, Polasani Samatha, Silver Raju, Prathama S. Mainkar, Raju Adepu, Srivari Chandrasekhar
Summary: The aryne insertion reaction with 2-aroyl malonates/cyanoesters leads to the formation of diarylmethane or chromones, depending on the substitution on the aryne ring. Chromones are generated when an electronegative atom is present at the ortho position of arynes, while other arynes undergo a cascade double aryne insertion to form diarylmethanes.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Chada Raji Reddy, Karna Nair, Amol D. Patil, Ramachandra Reddy Donthiri, Rene Gree
Summary: A novel one-pot base-promoted insertion reaction of indolyl 2-alkynes into a C-C single bond of 1,3-diketones, followed by intramolecular aldol reaction and dehydrative aromatization, has been described. This reaction cascade allows for the construction of 2-indolyl phenols, involving the formation of both C1-C2 and C3-C4 bonds of phenols with a good substrate range. Furthermore, these bifunctional compounds can be used in a novel arylative annulation in the presence of Grignard reagents to provide chromeno-indole frameworks.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Applied
Chada Raji Reddy, Muppidi Subbarao, Anjali Rathaur, Ejjirotu Srinivasu
Summary: This paper reports the Rh(III)-catalyzed cascade oxidative C-H functionalization/aza-annulation of indole and pyrrole-N-carboxamides with 1,3-enynes involving 1,4-rhodium migration. It provides an approach for the synthesis of imidazo[1,5-a]indol-3(2H)-ones from easily accessible substrates. The compatibility of sulfonamides in this method is also demonstrated, leading to the corresponding benzo[d]sultams.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Silver Raju, Palash Ghosh, Kiranmai Nayani, Jupally Prashanth, Balasubramanian Sridhar, Prathama S. Mainkar, Srivari Chandrasekhar
Summary: Cascade aza-Piancatelli reaction and [3+3]/[4+2] cycloaddition reactions can generate octahydro-4H-cyclopenta[b]pyridin-6-one scaffolds. In addition, octahydro-5,7a-epoxycyclopenta[cd]isoindol-4-one frameworks of gracilamine alkaloid and a novel decahydro-1H-dicyclopenta[cd,hi]isoindol-6-one can also be synthesized with excellent regio- and diastereo-selectivities.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Chada Raji Reddy, Uprety Ajaykumar, Dattahari H. Kolgave, Remya Ramesh
Summary: A variety of unactivated N-benzyl acrylamides underwent dearomative ipso-cyclization induced by sulfur-centered radicals in the presence of ceric ammonium nitrate as the oxidant to produce azaspirocycles in good yields. This represents the first report on ipso-dearomatization of N-benzyl acrylamides without substituents at the para-position of the aromatic ring. The reaction conditions are also applicable to substrates with substituents at the para-position such as F, NO2, OMe, OH, and OAc.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Chada Raji Reddy, Ankita Kumari, Suraj Aswale, Amol D. Patil, Y. Lakshmi Prapurna
Summary: The reaction of alkynyl p-quinone methide (pQM) with keto-methylenes through a base-mediated tandem 1,6-addition/annulation sequence, [2 + 3] annulation, affords furans for the first time. Various functionalized furans, including fused derivatives, can be obtained in good to excellent yields under mild reaction conditions. The effectiveness of alkynyl pQMs is demonstrated by their ability to access isoxazoles, pyrazoles via [3 + 2] annulation, and pyridines through [3 + 3] annulation in the presence of different bis-nucleophiles.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Chada Raji Reddy, Uprety Ajaykumar, Amol D. Patil, Remya Ramesh
Summary: A CAN-promoted oxidative ipso-cyclization of unactivated biaryl ynones with S-centered radicals has been developed for the synthesis of spiro[5,5]trienones. The method exhibited excellent regioselectivity towards spirocyclization and tolerated various functional groups. Dearomatization of previously unknown aryl/heteroaryl groups was also achieved. DMSO was employed as a low-toxicity, inexpensive solvent and oxygen source.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Chada Raji Reddy, Veeramalla Ganesh, Nagender Punna
Summary: This article describes a base-mediated unexpected aminative carbo-cyclization of cyano-enynyl esters, generated from Morita-Baylis-Hillman (MBH) acetates of propiolaldehydes, with secondary-amines. This metal-free reaction allows the synthesis of a unique cyclopentenone bearing an exocyclic double bond (cyano-olefin) with high E-selectivity in good yields. The synthetic potential of this annulation was further exemplified by the derivatization of bioactive molecules, a scale-up synthesis and synthetic transformations of the obtained cyclopentenone.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Kailas V. Preeti, Kailas V. Kallurkar, Prathama S. Mainkar, Raju Adepu, Srivari Chandrasekhar
Summary: A concise route for the synthesis of dihydrobenzo-[j]-phenanthridinones has been developed using an aryne annulation strategy under metal-free reaction conditions. The reaction involves multiple C-C and C-N bond cleavages/formations through Diels-Alder reaction, aromatization-driven C-N bond cleavage, and amide formation.
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)
