Article
Chemistry, Applied
Mark A. Bobko, Jennifer M. Elward, B. Narasimhulu Naidu, Yexenia E. Nieves-Quinones, Christopher A. Reiher, Qiaogong Su, Liang Sun, John Woodard, Shiping Xie, Wuxing Yang, Yunxing Yin
Summary: A new synthesis of allosteric HIV-1 integrase inhibitor GSK3839919A is reported, with a key advance in the synthesis of a crucial building block. The process development for the efficient multi-kilogram synthesis of GSK3839919A is also described, including optimization of Pd-catalyzed reactions and the use of lyophilization and gentisic acid.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2023)
Article
Chemistry, Organic
Peter Sunde-Brown, Ian D. Jenkins, Todd A. Houston
Summary: In this study, three different Mitsunobu reactions were investigated for the synthesis of 1-deoxymannojirimycin (1-DMJ). The highest yielding and most practical synthesis method was developed, which can be carried out on a 10 g scale with minimal chromatography.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Carlos Arambula, Joseph Rodrigues, Jung Jae Koh, Zachary Woydziak
Summary: This study presents a general and high-yielding method for producing 18 examples of rhodamines and rosamines from a single xanthone intermediate, with spectroscopic studies revealing trends in fluorophore efficiency based on substitution patterns at specific positions. This research provides insights for future designs of rhodamines/rosamines.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xavier Abel-Snape, Colton E. Johnson, Bianca Imbriaco, Mark Lautens
Summary: A palladium-catalyzed spirocyclization reaction was reported, which involved the insertion of an oxabicycle into a palladacycle. The reaction proceeded via carbocyclization and a C-H functionalization sequence, and the diastereoselective nature of the insertion was observed. The spirooxindoles produced in the reaction allowed for further transformations and were previously unaccessible.
Article
Chemistry, Organic
Nicholas W. See, Norbert Wimmer, Elizabeth H. Krenske, Vito Ferro
Summary: A new methodology has been developed for synthesizing other L-hexoses using a stereoselective approach, with beta-F at the anomeric position and a methoxycarbonyl substituent at C-6 identified as key factors to optimize selectivity for the L-hexose product. Additionally, the study has successfully established the shortest known synthetic route to a derivative of L-idose from a commercially available starting material.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Dror Ben Abba Amiel, Mattan Hurevich
Summary: In this study, high-shear mixing and stirring-based deprotection were employed for the expedient synthesis of a glycopeptide library.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
David L. Cain, Niall A. Anderson, David B. Cordes, Alexandra M. Z. Slawin, Allan J. B. Watson
Summary: A concise strategy for the total synthesis of several Aspidosperma alkaloids has been reported. The strategy involves a Suzuki-Miyaura cross-coupling and a Diels-Alder cascade reaction, leading to the synthesis of a common intermediate for Aspidosperma alkaloids. This intermediate has been successfully utilized for the synthesis of four different natural products.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sayan Mukherjee, Animesh Pramanik
Summary: A NCS-mediated methodology has been developed for rapid sulfenylation of enaminones of L-alpha-amino esters and aryl/alkyl amines at room temperature, producing a library of biologically important sulfenyl enaminones in good-to-excellent yields. This pathway generates sulfenyl chloride as an intermediate which leads to rapid sulfenylation of enaminones through cross-dehydrogenative coupling (CDC) under mild reaction conditions.
Article
Chemistry, Multidisciplinary
Carla Obradors, Benjamin Mitschke, Miles H. Aukland, Markus Leutzsch, Oleg Grossmann, Sebastian Brunen, Sebastian A. Schwengers, Benjamin List
Summary: Since early 2020, scientists have been striving to find effective solutions to combat SARS-CoV-2, focusing on developing reliable vaccines and repurposing drugs. However, the current synthetic routes for Remdesivir, the most widely used therapeutic during the early stages of infection, face challenges in cost-effective supply to patients. In this study, researchers have developed a straightforward method for adding (hetero)arenes to unprotected sugars, significantly expediting the synthesis of Remdesivir precursor GS-441524.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Letter
Acoustics
Ryoko Hara, Takahiro Iwami, Hiroshi Kashiwazaki, Akira Omoto
Summary: This letter presents a method of synthesizing musical instrument directivities by rotating a loudspeaker, and proposes a set of practical loudspeaker orientations named Step45 to reproduce the target directivity.
JOURNAL OF THE ACOUSTICAL SOCIETY OF AMERICA
(2021)
Article
Biochemistry & Molecular Biology
Jose C. Espinoza-Hicks, David Chavez-Flores, Gerardo Zaragoza-Galan, Alejandro A. Camacho-Davila
Summary: A synthetic strategy that is divergent and enantioselective has been reported for the production of non-proteinogenic, biologically active natural amino acids including norvaline, 5-hydroxy-4-oxo-L-norvaline, and γ-oxonorvaline. These compounds were synthesized with good yields (45-75%) starting from (S)-allylglycine obtained through asymmetric transfer allylation of glycine Schiff base using the Corey catalyst derived from cinchonidine in more than 97% enantiomeric excess.
Article
Chemistry, Organic
Michiel T. Uiterweerd, Adriaan J. Minnaard
Summary: The first total synthesis of the complex rearranged angucyclinones Elmonin and Pratenone A is reported in this study. The key naphthalene fragment present in both targets was efficiently prepared using peri-directed C-H functionalization. Coupling with two anisole-derived fragments led to the synthesis of the natural products, with Elmonin being prepared using a biomimetic spiro-ketalization.
Article
Multidisciplinary Sciences
Yun Bai, Huaiyu Wang, Jianghua He, Yuetao Zhang, Eugene Y. -X. Chen
Summary: The authors report the synthesis of well-defined PMMBL-based ABA tri-block copolymers with superior mechanical properties compared to PMMA-based counterparts, enabled by dual-initiating and living frustrated Lewis pairs. The PMMBL, a biobased acrylic polymer, shows enhanced properties over PMMA, particularly at high working temperatures, due to the unique synthesis method involving dual-initiating and living frustrated Lewis pairs.
NATURE COMMUNICATIONS
(2021)
Article
Biochemistry & Molecular Biology
Baoqin Cai, Marco Bocola, Ameng Zhou, Fenshuai Sun, Qing Xu, Jiadong Yang, Tianran Shen, Zhaoqi Zhang, Lei Sun, Yaoyao Ji, Yong Koy Bong, Thomas Daussmann, Haibin Chen
Summary: This study employs computer-aided directed evolution to enhance the activity, selectivity, and stability of L-threonine aldolase for the synthesis of (R,S)-AHNPA. The improved aldolase variant achieved a high conversion rate with cheap achiral precursors at a large scale.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Miao Zhang, Tingshu Wang, Chanyoung Boo, Sangho Koo
Summary: Versatile fluorescent polyaromatic compounds with alternating benzene and furan rings were synthesized and the effect of different substituents on the fluorescence intensity and wavelength was investigated.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Karen de la Vega-Hernandez, Fabrice Chemla, Franck Ferreira, Olivier Jackowski, Alejandro Perez-Luna
Summary: The stereoselective germylzincation of internal alkynes delivering trisubstituted vinylgermanes is achieved via a radical chain process, showing excellent regiocontrol for nonsymmetric substrates. Additionally, the germylzincation reaction can be combined with the Cu(I)-mediated electrophilic substitution of the C(sp(2))-Zn bond to obtain synthetically challenging tetrasubstituted vinylgermanes.
Article
Chemistry, Multidisciplinary
Seydou Kassamba, Alejandro Perez-Luna, Franck Ferreira, Muriel Durandetti
Summary: Intramolecular alkyne germylzincation allows for the synthesis of a diverse range of germoles from triarylhydrogermanes. The reaction involves the activation of Ge-H bond, leading to the formation of a heteroarylzinc intermediate, which can then undergo post-functionalization reactions.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Sebastien Curpanen, Giovanni Poli, Alejandro Perez-Luna, Julie Oble
Summary: Here we report a directed catalytic reaction for furfuryl imines, which allows access to versatile synthetic platforms. The reaction utilizes imines as directing groups and trialkylsilanes or bis(trimethylsilyl)methylsilane as silylating agents, in the presence of a hydride scavenger. Subsequently, fluoride-mediated activation strategies are applied to achieve a wide range of transformations and obtain high yields of products.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Alessia Mori, Sebastien Curpanen, Cristofer Pezzetta, Alejandro Perez-Luna, Giovanni Poli, Julie Oble
Summary: Furfural and related compounds, as building blocks of industrial interest, have gained attention as green alternatives to petroleum-derived compounds. This minireview summarizes the methods of direct C-H functionalization of furfurals without modifying the redox state of the aldehyde function, focusing on transition metal catalyzed functionalization of the heteroaromatic nucleus and C-H transformations of the aldehyde function.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Sebastien Curpanen, Per Reichert, Gabriele Lupidi, Giovanni Poli, Julie Oble, Alejandro Perez-Luna
Summary: 3-silylated furfurals are converted into 3-silylated 2-furyl carbinols upon condensation with organomagnesium or organolithium reagents. The hydroxy unit of the carbinol adducts can be exploited to promote C3(sp(2))-Si bond functionalization through intramolecular activation. This study introduces versatile platforms for the synthesis of 3-substituted 2-furyl carbinols from renewable feedstock.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Federico Banchini, Baptiste Leroux, Erwan Le Gall, Marc Presset, Olivier Jackowski, Fabrice Chemla, Alejandro Perez-Luna
Summary: 1,1-Bis(iodozincio)alkanes are used as dinucleophilic linchpins in an enantioselective double cross-coupling reaction sequence involving aryl iodides and then thioesters. This strategy, new in the area of asymmetric synthesis through two consecutive electrophilic substitution reactions of geminated C(sp(3))-organodimetallics, provides useful methodology to access acyclic alpha-disubstituted ketone products with high enantiomeric purity.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Organic
Ruben Perez Sevillano, Olivier Jackowski, Franck Ferreira
SYNTHESIS-STUTTGART
(2023)
Article
Materials Science, Multidisciplinary
Anthony Nina-Diogo, Benoit Bertrand, Serge Thorimbert, Geoffrey Gontard, Sehr Nassem-Kahn, Andrea Echeverri, Julia Contreras-Garcia, Clemence Allain, Gilles Lemercier, Eleonora Luppi, Candice Botuha
Summary: This report presents the design, synthesis, and photophysical study of two new series of promising fluorescent trisubstituted triazoles, PyOHTr and PyCOTr. The PyOHTr molecules were found to exhibit an excited state intramolecular proton transfer (ESIPT) fluorescence mechanism through ab initio theoretical calculations. These fluorescent dyes possess unique optical properties with potential applications in medicinal chemistry and materials science.
ADVANCED OPTICAL MATERIALS
(2023)
Article
Chemistry, Organic
Angel Palillero-Cisneros, Paola G. Gordillo-Guerra, Fernando Garcia-Alvarez, Olivier Jackowski, Franck Ferreira, Fabrice Chemla, Joel L. Teran, Alejandro Perez-Luna
Summary: We have demonstrated that alpha-(aminomethyl)acrylates are suitable for the 1,4-additions of dialkylzincs under aerobic conditions. This process involves a radical-polar crossover mechanism and represents a rare example of alkylzinc-group transfer to a tertiary alpha-carbonyl radical. The reaction can lead to the synthesis of enantioenriched beta 2-amino acids and beta 2,2-amino acids.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Anissa Beghennou, Geoffrey Gontard, Heloise Dossmann, Kevin Passador, Serge Thorimbert, Vincent Corce, Candice Botuha
Summary: Efficient synthesis of original 1,6-naphthyridin-7(6H)-ones and their optical properties, including dual fluorescence, solvatochromism, acidochromism, large Stokes shifts, and high quantum yields, are described in this study. These properties make them suitable for biological applications or as luminescent devices in materials science.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Seydou Kassamba, Mathias Reboli, Alejandro Perez-Luna, Franck Ferreira, Muriel Durandetti
Summary: Intramolecular addition of Ge-H bonds across internal alkynes was achieved for the first time, giving excellent yields (78-94%) and high regio- and stereoselectivities. The key step involves intramolecular germylzincation of arylgermane cores with C-C triple bonds. Reactivity of dialkylzincs towards Ge-H bonds was studied, showing syn addition to the alkyne. Cu-catalyzed electrophilic substitution allows the one-pot synthesis of tetrasubstituted vinylgermanes with retention of the C-C double bond geometry.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Andrea Echeverri, Candice Botuha, Tatiana Gomez, Eleonora Luppi, Julia Contreras-Garcia, Carlos Cardenas
Summary: Fluorescent probes that can sense the biological medium are extremely important in medical diagnostics. This paper showcases the in-silico design of potential fluorescent biomarkers that fulfill two important conditions - emission wavelength within the optical window of 650 to 950 nm and a large Stokes shift, greater than 150 nm.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
