Article
Chemistry, Organic
Shuheng Xu, Linwei Zeng, Sunliang Cui
Summary: The Diels-Alder (DA) reaction and hetero-Diels-Alder (HDA) reaction are powerful methods for constructing carbocycles and heterocycles. This study presents an integrated building block that combines both DA and HDA reactions, utilizing triazenyl dienes to undergo the DA reaction and the newly released alkene moiety and triazene to engage in the HDA reaction.
Article
Chemistry, Multidisciplinary
Shuang Qiu, Xin Zhang, Chaopeng Hu, Hongxu Chu, Qianli Li, David A. Ruiz, Liu Leo Liu, Chen-Ho Tung, Lingbing Kong
Summary: In this study, we reveal the reactivity of aryliminoboranes via BNCC π conjugation, enabling the dearomative Diels-Alder-like reactions with aldehydes. This reaction features mild conditions, catalyst-free, and exhibits a broad substrate scope and good functional group tolerance.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Guanghao Huang, Cyrille Kouklovsky, Aurelien de la Torre
Summary: The first enantioselective total synthesis of (+)-lucidumone is described, involving key steps such as an enantioselective inverse-electron-demand Diels-Alder cycloaddition and C-O bond formation. The synthesis is scalable and produced over one gram of natural product in one batch.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Physical
Bartosz Jedrzejewski, Mateusz Musiejuk, Justyna Doroszuk, Dariusz Witt
Summary: The study has developed simple and efficient methods for the synthesis of unsymmetrical vinyl disulfides with additional functional groups under mild conditions. These methods involve reactions between S-vinyl phosphorodithioate and thiotosylates, allowing for the synthesis of vinyl disulfides with various additional functionalities. Furthermore, the vinyl disulfides react with transient o-iminothioquinones in an inverse electron-demand [4+2] cycloaddition to yield benzo[b][1,4]thiazine derivatives.
Article
Chemistry, Multidisciplinary
Laura Cunningham, Patrick J. Guiry
Summary: This article describes the synthesis of planar chiral diols through a simple route, which are catalytically active and produce highly selective products in asymmetric reactions. The likely transition state is confirmed by X-ray crystallographic analysis, and both enantiomers of the product can be obtained by varying the substitution of the catalyst.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Marlene Fadel, Erick M. Carreira
Summary: The first total synthesis of (+)-pedrolide, a tigliane-derived diterpenoid featuring an unprecedented 5-5-6-6-3 carbon skeleton, was achieved. A key step in the synthesis involved the construction of the bicyclo[2.2.1]heptane core via an intramolecular cyclopentadiene-Diels-Alder cycloaddition. A norbornadiene was used as a surrogate for cyclopentadiene, and the unmasking of the cyclopentadiene was achieved through a complex Diels-Alder reaction cascade. This synthesis also provided a novel approach to a densely functionalized carane in an efficient and enantioselective manner.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Chemistry, Multidisciplinary
Victor Laina-Martin, Jose A. Fernandez-Salas, Jose Aleman
Summary: Cycloaddition reactions, particularly Diels-Alder reactions, are regarded as powerful methodologies for building carbon-carbon bonds. The inverse-electron-demand hetero-Diels-Alder reactions have been a significant breakthrough for synthesizing heterocyclic compounds. Among them, the organocatalytic enantioselective version has been extensively studied due to its asymmetric construction of diversely functionalized scaffolds under green chemistry conditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Gary L. Points, Christopher M. Beaudry
Summary: Substituted carbazoles are efficiently synthesized from 3-triflato-2-pyrones and alkynyl anilines, allowing for multiple substituents with complete control of regiochemistry, resulting in complex substitution patterns. This strategy can also be applied to prepare substituted bicarbazoles and related biaryls, and has been demonstrated in the synthesis of the carbazole natural product clausine C.
Article
Chemistry, Organic
Po Yuan, Tanja Gaich
Summary: In this study, we reported a synthetic method for the enantioselective and convergent total synthesis of (+)-pepluanol A, a natural product with a structurally intriguing skeleton. The method achieved high diastereoselectivity and convergency through key reactions for constructing the unique framework.
Article
Chemistry, Organic
Marco Corti, Marco Leusciatti, Mattia Moiola, Mariella Mella, Paolo Quadrelli
Summary: By mild oxidation of nitrile oxides with tertiary amine N-oxides, two new nitrosocarbonyl intermediates with carbohydrate-based chiral substituents were successfully synthesized and trapped, leading to hetero Diels-Alder cycloadducts and ene adducts from fair to excellent yields. The methodology shows promise in widening access to nitrosocarbonyls, versatile tools in organic synthesis, through easy conversion of aldoximes into hydroxymoyl halides.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Yukinori Kobayashi, Katsuya Namai, Kenta Watanabe, Akira Sasaki, Takuya Komatsu, Makoto Roppongi, Keitaro Yamamoto, Yutaka Ie, Satoshi Ito
Summary: It was found that replacing trimethylsilylacetylene with triisopropylsilylacetylene can improve the yield of 5-alkynyl bicycloporphyrins. The synthesized 5-alkynyl benzoporphyrins exhibit semiconductor characteristics, and other derivatives were synthesized through coupling and retro Diels-Alder reactions.
TETRAHEDRON LETTERS
(2021)
Article
Polymer Science
Aihemaiti Kayishaer, Mattia Annatelli, Chloe M. Hansom, Louis M. M. Mouterde, Aurelien A. M. Peru, Fabio Arico, Florent Allais, Sami Fadlallah
Summary: This study focuses on the synthesis of fully renewable polycarbonates using cellulose-based platform molecules. A solvent-free polymerization approach is utilized to obtain unique bio-based polycarbonates with high molecular weight and structural changes, paving the way for the development of functional materials with tunable properties.
MACROMOLECULAR RAPID COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Ju-Hyung Chae, Minyeong Choi, Semin Son, Su-Min Ko, In-Hwan Lee
Summary: Precise control of multiple structural parameters associated with vinyl polymers is important for producing materials with the desired properties and functions. The development of living polymerization methods has provided a way to control the various structural parameters of vinyl polymers, but controlling their sequence and regioregularity remains challenging. In this study, we report a scalable and modular synthesis of cyclic monomers through a one-step protocol using readily available vinyl precursors. The living cationic ring-opening polymerization of these cyclic monomers allows for the synthesis of vinyl polymers while controlling multiple factors, such as molecular weight, dispersity, alternating sequence, regioregularity, and end-group functionality. The synthesized vinyl polymers exhibit unique thermal properties and undergo fast photodegradation even under sunlight.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Tao Wang, Wen-Bin Wang, Yan-Ming Fu, Cheng-Feng Zhu, Lan-Jun Cheng, Yang-En You, Xiang Wu, You-Gui Li
Summary: An asymmetric double oxidative [3 + 2] cycloaddition is reported, which generates highly functionalized chiral CF3-containing spiro[pyrrolidin-3,2'-oxindole] with four contiguous stereocenters stereoselectively. This method directly constructs two C-C bonds from four C(sp3)-H bonds, and it features mild conditions, broad substrate scope, and excellent functional group compatibility.
Article
Chemistry, Multidisciplinary
Sarah A. French, Christopher J. Sumby, David M. Huang, Jonathan H. George
Summary: Inspired by a new biosynthetic hypothesis, a biomimetic total synthesis of atrachinenins A and B was achieved, explaining their racemic nature, and also suggesting a structure revision for atrachinenin C.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Biochemistry & Molecular Biology
Mijoon Lee, Zhenzhou Chen, Brittany N. Tomlinson, Major Gooyit, Dusan Hesek, Maria Raquel Juarez, Rasheeq Nizam, Bill Boggess, Elena Lastochkin, Valerie A. Schroeder, William R. Wolter, Mark A. Suckow, Jiancun Cui, Shahriar Mobashery, Zezong Gu, Mayland Chang
ACS CHEMICAL NEUROSCIENCE
(2015)
Article
Biochemical Research Methods
Kasey J. Clear, Kara M. Harmatys, Douglas R. Rice, William R. Wolter, Mark A. Suckow, Yuzhen Wang, Mary Rusckowski, Bradley D. Smith
BIOCONJUGATE CHEMISTRY
(2016)
Article
Chemistry, Medicinal
Edward Spink, Derong Ding, Zhihong Peng, Marc A. Boudreau, Erika Leemans, Elena Lastochkin, Wei Song, Katerina Lichtenwalter, Peter I. O'Daniel, Sebastian A. Testero, Hualiang Pi, Valerie A. Schroeder, William R. Wolter, Nuno T. Antunes, Mark A. Suckow, Sergei Vakulenko, Mayland Chang, Shahriar Mobashery
JOURNAL OF MEDICINAL CHEMISTRY
(2015)
Article
Chemistry, Multidisciplinary
Renee Bouley, Malika Kumarasiri, Zhihong Peng, Lisandro H. Otero, Wei Song, Mark A. Suckow, Valerie A. Schroeder, William R. Wolter, Elena Lastochkin, Nuno T. Antunes, Hualiang Pi, Sergei Vakulenko, Juan A. Hermoso, Mayland Chang, Shahriar Mobashery
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Biochemistry & Molecular Biology
Patrick R. Gonzales, Mitchell W. Pesesky, Renee Bouley, Anna Ballard, Brent A. Biddy, Mark A. Suckow, William R. Wolter, Valerie A. Schroeder, Carey-Ann D. Burnham, Shahriar Mobashery, Mayland Chang, Gautam Dantas
NATURE CHEMICAL BIOLOGY
(2015)
Article
Multidisciplinary Sciences
Ming Gao, Trung T. Nguyen, Mark A. Suckow, William R. Wolter, Major Gooyit, Shahriar Mobashery, Mayland Chang
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2015)
Article
Microbiology
Joon Lee, Woo Yang, Andrew Hostetler, Nathan Schultz, Mark A. Suckow, Kay L. Stewart, Daniel D. Kim, Hyung Soo Kim
Article
Chemistry, Medicinal
Renee Bouley, Derong Ding, Zhihong Peng, Maria Bastian, Elena Lastochkin, Wei Song, Mark A. Suckow, Valerie A. Schroeder, William R. Wolter, Shahriar Mobashery, Mayland Chang
JOURNAL OF MEDICINAL CHEMISTRY
(2016)
Article
Oncology
Jonathan D. Ashley, Charissa J. Quinlan, Valerie A. Schroeder, Mark A. Suckow, Vincenzo J. Pizzuti, Tanyel Kiziltepe, Basar Bilgicer
MOLECULAR CANCER THERAPEUTICS
(2016)
Article
Biochemistry & Molecular Biology
Major Gooyit, Zhihong Peng, William R. Wolter, Hualiang Pi, Derong Ding, Dusan Hesek, Mijoon Lee, Bill Boggess, Matthew M. Champion, Mark A. Suckow, Shahriar Mobashery, Mayland Chang
ACS CHEMICAL BIOLOGY
(2014)
Article
Chemistry, Multidisciplinary
Jonathan D. Ashley, Jared F. Stefanick, Valerie A. Schroeder, Mark A. Suckow, Nathan J. Alves, Rikio Suzuki, Shohei Kikuchi, Teru Hideshima, Kenneth C. Anderson, Tanyel Kiziltepe, Basar Bilgicer
JOURNAL OF CONTROLLED RELEASE
(2014)
Article
Chemistry, Medicinal
Jonathan D. Ashley, Jared F. Stefanick, Valerie A. Schroeder, Mark A. Suckow, Tanyel Kiziltepe, Basar Bilgicer
JOURNAL OF MEDICINAL CHEMISTRY
(2014)
Article
Chemistry, Multidisciplinary
Peter I. O'Daniel, Zhihong Peng, Hualiang Pi, Sebastian A. Testero, Derong Ding, Edward Spink, Erika Leemans, Marc A. Boudreau, Takao Yamaguchi, Valerie A. Schroeder, William R. Wolter, Leticia I. Llarrull, Wei Song, Elena Lastochkin, Malika Kumarasiri, Nuno T. Antunes, Mana Espahbodi, Katerina Lichtenwalter, Mark A. Suckow, Sergei Vakulenko, Shahriar Mobashery, Mayland Chang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Article
Multidisciplinary Sciences
Bridgette D. Semple, Linda J. Noble-Haeusslein, Major Gooyit, Kayleen G. Tercovich, Zhihong Peng, Trung T. Nguyen, Valerie A. Schroeder, Mark A. Suckow, Mayland Chang, Jacob Raber, Alpa Trivedi
Article
Veterinary Sciences
Kay L. Stewart, Mark A. Suckow
JOURNAL OF THE AMERICAN ASSOCIATION FOR LABORATORY ANIMAL SCIENCE
(2016)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)