Article
Chemistry, Organic
Zhi Zhang, Liansuo Zu
Summary: The study successfully synthesized a steroid-sterigmatocystin heterodimer using a concise method, including cascade dialdehyde cyclization, phenol-assisted reductive alkylation, and SNAr reaction. The research also explored a glycosylation-inspired method to provide the acetal linkage with ergosterol peroxide.
Article
Chemistry, Multidisciplinary
Kosuke Okada, Ken-ichi Ojima, Hirofumi Ueda, Hidetoshi Tokuyama
Summary: The synthesis of (+)-pleiocarpamine, (+)-voacalgine A and (+)-bipleiophylline was achieved in this study. The 10-step synthesis of (+)-pleiocarpamine features the construction of stereochemistry at the C16 position by radical cyclization and the synthesis of the highly strained cage-like structure via Pd-catalyzed intramolecular aromatic C-H functionalization. By modifying the biomimetic aerobic oxidative coupling of tryptophane derivatives catalyzed by FePc(CO2H)(8), the oxidative coupling of (+)-pleiocarpamine with pyrocatechuic acid produced (+)-voacalgine A. The total synthesis of (+)-bipleiophylline was completed by the second coupling of (+)-voacalgine A with (+)-pleiocarpamine or the one-pot couplings of 2 equiv of (+)-pleiocarpamine with pyrocatechuic acid.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Hesi Yang, Yan Zhang, Wei Chen, Hongliang Shi, Liang Huo, Jia Li, Huilin Li, Xingang Xie, Xuegong She
Summary: This article describes the first total syntheses of two novel ansamacrolactams, (+/-)-catellatolactams A and B, in 5 and 8 steps, respectively. The synthesis strategy involves an amidation reaction, a regioselective C-H insertion, and an RCM reaction to form the macrocycles with E-olefin. The concise and scalable synthesis provided over 200 mg of the target molecules.
Article
Chemistry, Multidisciplinary
Robert F. Lusi, Goh Sennari, Richmond Sarpong
Summary: A strategy orthogonal to classic approaches and coupled with C-H functionalization methods has been used to achieve the shortest synthesis and divergent syntheses of a sesquiterpenoid longiborneol, providing inspiration for the synthesis of other topologically complex natural products.
Article
Chemistry, Multidisciplinary
Lukas Anton Wein, Klaus Wurst, Thomas Magauer
Summary: The study presented the construction of seven novel ent-trachylobane diterpenoids using a bioinspired synthetic strategy. Enantioselective and scalable access to five ent-trachylobanes was achieved in the first phase, with one compound produced on a 300 mg scale. Chemical C-H oxidation methods were then used in the second phase to selectively convert two higher functionalized ent-trachylobanes, revealing the potential and limitations of established protocols for complex molecule synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
In-Soo Myeong, Nadide Hazal Avci, Mohammad Movassaghi
Summary: The first total synthesis of (-)-kopsifoline A and (+)-kopsifoline E was achieved in this study, featuring a biogenetically inspired regioselective C17-functionalization strategy for a versatile intermediate. The vinylogous urethane substructure of the intermediate allowed for the synthesis of (-)-kopsifoline D via C3-C21 bond formation under Mitsunobu reaction conditions, as well as selective C17-functionalization en route to (-)-kopsifoline A and (+)-kopsifoline E.
Article
Chemistry, Multidisciplinary
Lilla Koser, Thorsten Bach
Summary: The first total synthesis of (-)-5-deoxyenterocin has been accomplished, starting from pentane-1,3,5-triol with a linear sequence of 16 steps and an overall yield of 0.2%. Key steps of the synthesis include aldol reactions, hydroxylation reactions, and an intramolecular aldol reaction. Despite attempts, a functionalization reaction at position C5 was unsuccessful.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Haidi Tang, Muliang Zhang, Yuchao Zhang, Penghao Luo, Davide Ravelli, Jie Wu
Summary: Researchers have developed a method for synthesizing thioesters through carbonyl thiyl radical-based reactions, using direct photocatalyzed hydrogen atom transfer. This method allows for the synthesis of complex pharmaceutical molecules from readily available commodity chemicals. The study provides a new approach for the application of thiol-ene click chemistry in organic synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Adriana Recoba-Torres, Silvano Cruz-Gregorio, Leticia Quintero, Jacinto Sandoval-Lira, Julio Romero-Ibanez, Fernando Sartillo-Piscil
Summary: This report presents a new synthesis strategy for the direct deconstruction of a tetracyclic indoloquinolizine motif into the scaffold of a naturally occurring alkaloid, without the need for transition or precious metals.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Emily K. Kirkeby, Zachary T. Schwartz, Myles A. Lovasz, Andrew G. Roberts
Summary: This article presents a concise strategy for preparing polycyclic heteroaromatics through a deaminative contraction cascade. The efficient deaminative ring contraction involves the methylation and rearrangement/dehydroamination of a biaryl-linked dihydroazepine. The presence of pseudosymmetry guides the retrosynthetic analysis and allows for the construction of pyridyl-containing polycyclic heteroaromatics.
Article
Chemistry, Multidisciplinary
Emily K. Kirkeby, Zachary T. Schwartz, Myles A. Lovasz, Andrew G. Roberts
Summary: This article details a concise strategy to prepare polycyclic heteroaromatics through a deaminative contraction cascade. The efficient deaminative ring contraction involves the methylation of a biaryl-linked dihydroazepine to form a cyclic ammonium cation, followed by a base-induced [1,2]-Stevens rearrangement/dehydroamination sequence. The presence of pseudosymmetry guides the retrosynthetic analysis of pyridyl-containing polycyclic heteroaromatics, enabling their construction through reductive cyclization and deaminative contraction of tertiary amine precursors.
Article
Chemistry, Organic
Ze-Jun Xu, Xu-Yuan Liu, Ming-Zhu Zhu, Yu-Liang Xu, Yue Yu, Hai-Ruo Xu, Ai-Xia Cheng, Hong-Xiang Lou
Summary: In this study, two types of photoredox-catalyzed cascade reactions using diaryliodonium salts were developed for the concise synthesis of norascyronone A and beta-eudesmol. A rationally designed photoredox-catalyzed arylation/cyclization/Friedel-Crafts cascade reaction was used for the norascyronone synthesis, while a visible-light-induced radical cyclization/acyloxy-migration reaction was explored for the eudesmol synthesis, with mechanistic studies indicating initiation by one-electron oxidation of the enol ester.
Article
Chemistry, Multidisciplinary
Ping Zhao, Yun Guo, Xinjun Luan
Summary: This study presents a concise total synthesis of Dalesconol A through a polycyclization/oxidation approach, involving key steps of polycyclization and oxidation state adjustments.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Si-Hua Hou, Adriana Y. Prichina, Guangbin Dong
Summary: The development of a deconstructive strategy for the first asymmetric synthesis of (-)-thebainone A was described, utilizing an enantioselective C-C bond activation and a C-O bond cleavage reaction. The newly optimized conditions show broad substrate scope and excellent enantioselectivity (up to 99.5:0.5 er). The synthesis of (-)-thebainone A was completed by taking advantage of boron-mediated ether bond cleavage through two complementary routes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Manjunatha Vishwanath, Chhabi Lal Chaudhary, Yunjeong Park, Mayavan Viji, Chanhyun Jung, Kwanghee Lee, Jaeuk Sim, Seong Min Hong, Da Hye Yoon, Dae Hee Lee, Jae Kang Lee, Heesoon Lee, Mi Kyeong Lee, Sun Yeou Kim, Jae-Kyung Jung
Summary: Secondary metabolites from Hericium erinaceus have neurotrophic and neuroprotective effects. The total synthesis of Isohericerinol A (1) and its regioisomer 5 was successfully achieved, and both compounds showed potent neurotrophic activity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Timaeus E. F. Morgan, Leanne M. Riley, Adriana A. S. Tavares, Andrew Sutherland
Summary: This study developed two synthetic routes that allow highly selective radiofluorination reactions and rapid deprotection of precursors under mild acidic conditions, improving the synthesis of positron emission tomography imaging agents.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Amy C. Dodds, Andrew Sutherland
Summary: A mild and regioselective method for the preparation of unsymmetrical biaryl sulfides using iron(III) catalysis was described. The method was applicable for late-stage thiolation of tyrosine and tryptophan derivatives, and was used for the synthesis of pharmaceutically relevant compounds. Kinetic studies revealed differences in the reaction mechanism depending on the electronic properties of the arenes.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Amy C. Dodds, Andrew Sutherland
Summary: Phenoxathiins are an important class of sulfur-containing heterocycle, and we report a two-step synthesis method using iron and copper-mediated reactions, which can avoid complex starting materials, harsh conditions, or precious transition metals.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Lachlan J. N. Waddella, Martyn C. Henry, Mohamed A. B. Mostafa, Andrew Sutherland
Summary: A one-pot, two-stage synthesis of diaryl sulfonamides using sequential iron and copper catalysis has been developed. This method allows for the regioselective iodination and N-arylation of activated arenes and is applicable for the synthesis of various compounds.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Holly McErlain, Euan B. McLean, Timaeus E. F. Morgan, Valeria K. Burianova, Adriana A. S. Tavares, Andrew Sutherland
Summary: Heterocyclic nonacetamide ligands, including SynVesT-1, have potential applications as positron emission tomography (PET) imaging agents for the synaptic vesicle glycoprotein 2A (SV2A). This study demonstrates the asymmetric synthesis of SynVesT-1 using iminium organocatalysis, involving the conjugate addition of nitromethane with a cinnamaldehyde and subsequent reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Nanoscience & Nanotechnology
Victor Tabouillot, Rahul Kumar, Paula L. Lalaguna, Maryam Hajji, Rebecca Clarke, Affar S. Karimullah, Andrew R. Thomson, Andrew Sutherland, Nikolaj Gadegaard, Shun Hashiyada, Malcolm Kadodwala
Summary: In this study, we harness the power of nanophotonic platforms and plasmonic circularly polarized luminescence (PCPL) to detect the chirality of monolayer quantities of a de novo designed peptide. This demonstrates that optimal biomolecular detection performance can be achieved by leveraging the near field sensitivity of PCPL, opening new avenues for nanometrology.
Article
Chemistry, Organic
Lachlan J. N. Waddell, Maisie R. Senkans, Andrew Sutherland
Summary: Aryl thiocyanates are versatile synthetic intermediates for the preparation of diverse arene building blocks in medicinal chemistry. We developed a fast and efficient Lewis acid-catalyzed method for regioselective thiocyanation of arenes. Iron(III) chloride was found to be an effective Lewis acid for activating N-thiocyanatosaccharin and subsequent thiocyanation of activated arenes, including biologically active compounds such as metaxalone and an estradiol derivative. This method was also used in a one-pot tandem iron-catalytic process for regioselective, dual functionalization of an arene building block.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Amy C. Dodds, Lachlan J. N. Waddell, Andrew Sutherland
Summary: In this study, we developed a highly active super Lewis acid, iron(III) triflimide, as an activating agent for the selective functionalization of arenes. By combining iron(III)-catalyzed halogenation reactions with copper(I)-catalyzed Ullmann-type coupling reactions, we achieved one-pot, multistep processes and demonstrated intermolecular aryl C-H amination. Furthermore, we successfully applied these methods to the synthesis of benzannulated heterocycles, biologically active compounds, and natural products.
Review
Biochemistry & Molecular Biology
Robert A. Hill, Andrew Sutherland
Summary: This article presents a personal selection of 32 recent papers that cover various aspects of current developments in bioorganic chemistry and novel natural products, such as strophioblin from Strophioblachia fimbricalyx.
NATURAL PRODUCT REPORTS
(2023)
Article
Chemistry, Organic
Amy C. Dodds, Sabrina Puddu, Andrew Sutherland
Summary: A two-step synthesis of phenothiazines has been developed using a dual-catalytic ortho-thioarylation reaction of anilines as the key step. The activation of N-(2-bromophenylthio)succinimide was achieved using a super Lewis acid and a Lewis base, resulting in an efficient ortho-thioarylation reaction of various protected aniline derivatives and less reactive, unprotected analogues. The thioarylated adducts were then cyclised to the desired phenothiazines using either an Ullmann-Goldberg or Buchwald-Hartwig coupling reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Biochemistry & Molecular Biology
Robert A. Hill, Andrew Sutherland
Summary: This article presents a personal selection of 32 recent papers covering various aspects of current developments in bioorganic chemistry and novel natural products, such as asporychalasin from Aspergillus oryzae.
NATURAL PRODUCT REPORTS
(2021)
Review
Biochemistry & Molecular Biology
Robert A. Hill, Andrew Sutherland
Summary: This article presents a personal selection of 32 recent papers covering various aspects of current developments in bioorganic chemistry and novel natural products, including chlorahupetone A from Chloranthus henryi var. hupehensis.
NATURAL PRODUCT REPORTS
(2021)
Article
Chemistry, Organic
Rochelle McGrory, Reka J. Faggyas, Andrew Sutherland
Summary: A mild and effective one-pot synthesis method has been developed for 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues. The method is compatible with a wide range of functional groups and substituents and has been successfully applied for the synthesis of pharmaceutically important targets.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Biochemistry & Molecular Biology
Robert A. Hill, Andrew Sutherland
Summary: This paper presents a personal selection of 32 recent papers covering various aspects of current developments in bioorganic chemistry and novel natural products, including eurysoloid A from Eurysolen gracilis.
NATURAL PRODUCT REPORTS
(2021)
Article
Nanoscience & Nanotechnology
Victor Tabouillot, Rahul Kumar, Paula L. Lalaguna, Maryam Hajji, Rebecca Clarke, Affar S. Karimullah, Andrew R. Thomson, Andrew Sutherland, Nikolaj Gadegaard, Shun Hashiyada, Malcolm Kadodwala
Summary: The use of plasmonic circularly polarized luminescence (PCPL) as a local probe on nanophotonic platforms enables chiral detection of trace biological molecules with higher sensitivity than far field optical measurements.
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)
