Article
Chemistry, Organic
Su-Yu Huang, Long-Hui Gao, Xiong-Zhi Huang, Pei-Qiang Huang
Summary: This article provides a detailed account of the synthetic efforts towards the enantioselective total synthesis of the complex alkaloid methoxystemofoline. The key steps include Keck allylation, olefin cross-metathesis, regioselective aldol addition, and Overman's method for moiety installation. The final step resulted in the formation of both the proposed structure of methoxystemofoline and its E-stereoisomer in a 1:1 ratio, leading to the suggestion to rename the natural product as isomethoxystemofoline.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yuki Kimura, Eisaku Ohashi, Sangita Karanjit, Takashi Taniguchi, Atsushi Nakayama, Hiroshi Imagawa, Ryota Sato, Kosuke Namba
Summary: The total syntheses of two natural products, 4,10-dihydroxy-8,12-guaianolides, were achieved. The construction of the typical 5,7-fused system of 8,12-guaianolides using a ring expansion reaction revealed that the previously reported structures of both natural products were incorrect.
Article
Chemistry, Multidisciplinary
Xiao-Wei Chen, Zi-Chao Hou, Chi Chen, Ling-Hui Zhang, Meng-En Chen, Fu-Min Zhang
Summary: The first enantioselective total syntheses of six natural and two proposed meroterpenoids from Psoralea corylifolia have been achieved in 7-9 steps from 2-methylcyclohexanone. These synthetic approaches offer a high level of flexibility, stereodivergent fashion, and short route, providing a potential platform for the preparation of various this-type meroterpenoids and their pseudo-natural products.
Article
Chemistry, Medicinal
Arun K. Ghosh, Hao Yuan
Summary: This study focuses on the enantioselective syntheses and structural analysis of cytotoxic agents from marine dinoflagellates. The correct structures of the compounds were assigned through detailed analysis of spectral data. However, the synthetic compounds did not exhibit significant cytotoxic properties in preliminary biological evaluation.
Article
Chemistry, Multidisciplinary
Wenqiang Zhou, Tao Zhou, Mengxing Tian, Yan Jiang, Jiaojiao Yang, Shuai Lei, Qi Wang, Chongzhou Zhang, Hanyue Qiu, Ling He, Zhen Wang, Jun Deng, Min Zhang
Summary: Through the development of a new method and key reactions, the concise, collective, and asymmetric total syntheses of four schizozygane alkaloids, including the first asymmetric synthesis, have been achieved in only 11-12 steps from tryptamines.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Raphael J. Zachmann, Kenzo Yahata, Mira Holzheimer, Maxime Jarret, Cornelia Wirtz, Alois Fuerstner
Summary: The structure of prorocentin has been revised through a flexible synthesis approach, showing that the previously proposed structure is incorrect. The new, more plausible structure was obtained using methods such as gold-catalyzed spirocyclization reactions. This study has important implications for the understanding of prorocentin's structure.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Masafumi Nishiumi, Tadachika Miyasaka, Masaatsu Adachi, Toshio Nishikawa
Summary: The collective synthesis of four spiro-cyclic guanidines isolated from puffer fish, which are considered possible biosynthetic intermediates of tetrodotoxin, has been achieved through stepwise deoxygenation or hydroxylation of a common intermediate.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Akira Hirose, Ayumu Watanabe, Kohei Ogino, Masanori Nagatomo, Masayuki Inoue
Summary: Rhamnofolane, tigliane, and daphnane diterpenoids are structurally complex natural products with multiple oxygen functionalities, and a new synthetic strategy was developed for the total syntheses of five representative members of these families. This unified synthetic route required only 16-20 total steps, demonstrating exceptional efficiency.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Roberto Serrano, Yaroslav D. Boyko, Lucas W. Hernandez, Aleksandras Lotuzas, David Sarlah
Summary: The concise total syntheses of oxidized norcembranoid terpenoids (-)-scabrolide A and (-)-yonarolide have been achieved in 10 and 11 steps, respectively, by integrating two chiral-pool-derived fragments, including a [5,5]-bicyclic lactone accessed through a powerful Ni-catalyzed pentannulation of functionalized cyclopentenone with methylenecyclopropane and subsequent fragmentation. Additional features included a Liebeskind-Srogl coupling, induction of a cyclization/elimination cascade by a zinc-amido base, and installation of a sensitive enedione motif by latestage ?-oxidation.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Xinpei Cai, Lei Li, Ye-Cheng Wang, Jianhan Zhou, Mingji Dai
Summary: In this paper, we describe the complete synthesis of phleghenrines A and C from commercially available starting materials in 7 and 8 steps, respectively. Key steps include an inverse electron-demand Diels-Alder reaction between a masked o-benzoquinone and a N-protected enamine to generate a bicyclo[2.2.2]octenone core, a Bu''chner-Curtius-Schlotterbeck one-carbon insertion to expand the bicyclo[2.2.2]octenone to a bicyclo[3.2.2]nonenone, and Trauner's modified 2-pyridone synthesis to install the 2-pyridone moiety.
Article
Chemistry, Organic
Yingjie Wang, Biao Yu
Summary: The total syntheses of two antiangiogenic anthraquinone glycosides, aturanosides A and B, were achieved in an expeditious manner, emphasizing anthraquinone synthesis, phenol glycosylation, alpha-D-glucosaminoside installation, and judicious use of protecting groups.
Article
Chemistry, Organic
Day-Shin Hsu, Meng-Yu Wang, Jiun-Yi Huang
Summary: The asymmetric total syntheses of (+)-5-epi-schisansphenin B and the proposed structure of (+)-15-hydroxyacora4(14),8-diene have been successfully accomplished in eight synthetic steps from 1,3-cyclopentadione. The enantioselective palladium-catalyzed redox-relay Heck alkenylation, the intramolecular Stetter reaction, and the regioselective Tiffeneau-Demjanov-type ring expansion played crucial roles in these syntheses.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Baiyang Jiang, Mingji Dai
Summary: We report the total syntheses of four hamigeran natural products with a 6-7-5 tricyclic carbon skeleton. A palladium-catalyzed intramolecular cyclopropanol ring-opening cross-coupling was used to build the central seven-membered ring, and a series of oxidations, including a challenging aromatic C-H oxidation, were employed to introduce the peripheral functionalities. This approach allowed us to achieve the first total syntheses of hamigeran C (14 steps), debromohamigeran I (12 steps), hamigeran I (13 steps), and hamigeran G (13 steps), significantly shorter than the previously reported longest linear sequence (24 steps).
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Ming Wang, Ya Wu, Mei Xu, Sheng Liu
Summary: An efficient synthetic route to iheyamine A and its analogues was discovered, involving a crucial one-pot transformation that included C-C migration to form the characteristic seven-membered ring. Subsequent addition of acetone to iheyamine A initiated a cascade process to complete the total synthesis of iheyamine B.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ming Wang, Ya Wu, Mei Xu, Sheng Liu
Summary: An efficient synthetic route to iheyamine A and its analogues was discovered, involving a crucial one-pot transformation with C-C migration to form the characteristic seven-membered ring. The subsequent addition of acetone to iheyamine A initiated a cascade process leading to the complete total synthesis of iheyamine B.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Kishore Kumar Palli, Palash Ghosh, Shiva Krishna Avula, B. Sridhara Shanmukha Rao, Amol D. Patil, Subhash Ghosh, Gangarajula Sudhakar, Chada Raji Reddy, Prathama S. Mainkar, Srivari Chandrasekhar
Summary: Remdesivir, the first drug approved by the FDA to treat COVID-19, is highly demanded for patients infected with the SARS-CoV-2 virus. A facile approach minimizing protecting group manipulations to afford remdesivir in good overall yield is reported in this study.
TETRAHEDRON LETTERS
(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, Applied
Chada Raji Reddy, Roshan Chandrakant Kajare, Nagender Punna
Summary: Herein, we report the synthesis of functionalized dihydro-benzo[b]fluorenones through a manganese-mediated cascade radical cyclization method. The method features high atom- and step-economy, and allows for the construction of three new C-C bonds with high yields under mild reaction conditions, demonstrating the synthetic efficacy of the developed method.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
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, 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
Chada Raji Reddy, Dattahari H. Kolgave, Uprety Ajaykumar, Remya Ramesh
Summary: A copper-catalyzed ipso-annulation reaction of N-(p-methoxyaryl)propiolamides with 1,3-diketones has been developed, enabling the synthesis of diketoalkylated spiro[4.5]trienones and spiro[5.5]trienones.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Chada Raji Reddy, Mayur C. Bhandari, Amol D. Patil, Mounika Aila, Ramachandra Reddy Donthiri
Summary: An efficient selenylative cyclization of aryl-alkynones with diselenides in the presence of iron(iii)chloride at room temperature to prepare 3-seleno-2-naphthols in good yields has been described. Furthermore, the resulting products were transformed into selenyl-naphthofuran and selenyl-1,2-naphthoquinone derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
