Article
Chemistry, Organic
Nashvin Mikhail Singh Deepak, Andrei G. Kutateladze, Mikhail Elyashberg, Craig M. Williams, Roderick W. Bates
Summary: The proposed structure of arneroma B has been revised from a cyclopentadienone to a 2,4-disubstituted furan. The reassignment has been confirmed by total synthesis of the revised structure.
Article
Chemistry, Medicinal
Fusong Wu, Tao Zhang, Jie Yu, Yian Guo, Tao Ye
Summary: The asymmetric total synthesis of four diastereomers of laingolide A enabled the unambiguous assignment of the natural product's stereochemistry. The key features of the convergent, fully stereocontrolled approach included a copper-catalysed stereospecific Kumada-type coupling, a Julia-Kocienski olefination, and an RCM/alkene migration sequence to obtain the desired macrocyclic enamide.
Article
Plant Sciences
Injae Song, Hyewon Lim, Simin Chun, Seok Beom Lee, Jungmoo Huh, Dong-Chan Oh, Suckchang Hong
Summary: The first total synthesis of gaylussacin was reported in this study, along with the synthesis of its derivatives. Heck cross-coupling was used as a key step to introduce the stilbene moiety.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Chemistry, Organic
Junyang Liu, Ying Chen, Hendrik Luesch, Tao Ye
Summary: The first asymmetric total synthesis and validation of the structural assignment of des-thiomethyllooekeyolide A (3) is described, which involves a Shiina macrolactonization and a late-stage pyran-hemiketal formation. The eight stereogenic centers of the C16-polyketide chain were installed by sequential aldol and crotylation reactions.
Article
Plant Sciences
Tao Sheng, Caiyun Ma, Guangyan Zhang, Xuan Pan, Zhanzhu Liu
Summary: The first total synthesis of griseofamine B was achieved starting from L-4-bromo tryptophan methyl ester hydrochloride via five steps, with an overall yield of 18%. Three stereoisomers of griseofamine B were also synthesized using the same procedure, with yields of 5%, 19%, and 5% respectively. In vitro antibacterial activities were evaluated, and all four compounds exhibited lower activity than griseofamine A.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Chemistry, Organic
Chinatsu Ono-Ogasawara, Shunya Yamamoto, Yusuke Ogura, Hironori Okamura, Kiyofumi Takaba, Satoshi Yoshida, Sota Sato, Koji Yonekura, Hirosato Takikawa
Summary: Strigolactones are a class of rhizosphere semiochemicals and plant hormones, characterized by a tricyclic lactone (ABC ring) and a butenolide (D ring) as their basic skeleton. Zeapyranolactone, a noncanonical strigolactone isolated from maize, has been synthesized for the first time as a racemic and diastereomeric mixture, and its stereochemistry has been determined by three-dimensional electron diffraction crystallography as 4S*, 4aS*, 2'R*. The synthetic route developed is straightforward and does not require typical protective groups.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Organic
Ying Xiong, Yong-Hong Chen, Tao Li, Jian-Hua Xie, Qi-Lin Zhou
Summary: Here, we present the first enantioselective total synthesis of the highly complex hamigeran diterpenoid (-)-hamigeran F and its rearrangement product, which involves key steps of asymmetric hydrogenation, Horner-Wadsworth-Emmons olefination, and intramolecular Friedel-Crafts acylation to construct a [6,6,5]-tricyclic skeleton bearing three consecutive stereocenters. The synthesis also includes Rosenmund reduction, Wittig reaction, dihydroxylation to assemble the alpha-acetoxy ketone group, and an intramolecular aldol reaction to build the tetracyclic core structure.
Article
Chemistry, Organic
Harry B. Hicks, Daniel S. Brown, Hau Sun Sam Chan, Bruno A. Sousa, Kirsten E. Christensen, Jonathan W. Burton
Summary: In this study, the synthesis of both (E)-ocellenyne and (Z)-ocellenyne was reported, and their absolute configuration was determined through single crystal X-ray diffraction studies. The configuration of the syn-12,13-dibromide was found to be (S, S), supporting the proposed biogenesis from the (6S, 7S)-laurediols.
Article
Chemistry, Multidisciplinary
Jyoti Shukla, Manoj Kumar Gangwar, Dipankar Koley
Summary: The total synthesis of (-)-delta-lycorane is achieved through organocatalytic Mannich reaction and diastereoselective conjugate addition. Various reactions including Bischler-Napieralski reaction and ring closing metathesis are utilized.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Marc Paul Beller, Sergei Ivlev, Ulrich Koert
Summary: A stereoselective synthesis method for the proposed and actual structures of natural products preussochromones E and F is reported. The key step involves a ring-closing metathesis reaction to form a five-membered ring and install the trans configuration of the annulated five-six membered ring system. Analysis of the (3)J NMR couplings between the isolated natural product and the synthesized compound revealed the cis annulation in its real structure, which can also be synthesized using an intramolecular aldol reaction.
Article
Chemistry, Organic
Hongbo Dong, Min Wu, Weihong Du, Mingwei Shong, Yujiao He, Yuchi Wang
Summary: In this study, total syntheses of both forms of Millpuline B were reported for the first time, with key steps involving Grignard reaction and asymmetric CBS reduction. The enantiomeric excess of the synthesized compound reached up to 94.3%, and the Mosher's methods were used to determine the absolute configuration of key intermediates.
SYNTHETIC COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Naoaki Kurisawa, Arihiro Iwasaki, Kazuya Teranuma, Shingo Dan, Chikashi Toyoshima, Masaru Hashimoto, Kiyotake Suenaga
Summary: In this study, a new SERCA inhibitor, iezoside (1), isolated from the marine cyanobacterium Leptochromothrix valpauliae, is reported. Iezoside (1) is the second-strongest SERCA inhibitor known to date, with a structure fundamentally different from any other SERCA inhibitor, and the highest potency among marine natural products (K_i 7.1 nM). The comprehensive analysis of iezoside (1), including its isolation, structural characterization supported by density functional theory (DFT) calculations and statistical analysis, total synthesis, and clarification of the mode of action of its potent antiproliferative activity (IC50 6.7 +/- 0.4 nM against HeLa cells), is described.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Hongyuan Zhang, Haibing He, Shuanhu Gao
Summary: The asymmetric synthesis of the complex C-18 Cephalotaxus dinorditerpenoid cephanolide B was achieved for the first time using a remote hydroxyl group directed hydrogenation strategy and a sequence of modified transformations. The key hexahydrofluorenone core skeleton and selective reductions were crucial in achieving the target compound.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Shinnosuke Okazaki, Kaho Senda, Ayaka Tokuta, Misa Inagaki, Kazuo Kamaike, Koichiro Ota, Hiroaki Miyaoka
Summary: This article reports the total synthesis of natural polyketides plakortone Q and plakdiepoxide isolated from a marine sponge. The efficient synthesis was achieved through a protecting-group-free strategy. This research is of great importance for the development of new drugs with broad pharmacological activities.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xiao-Long Lu, Yuanyou Qiu, Baochao Yang, Haibing He, Shuanhu Gao
Summary: The asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B was achieved in 6-7 steps using an easily accessible meso-cyclohexadienone derivative. The strategy provides a scalable route to prepare target molecules and their derivatives for further biological studies.
Article
Plant Sciences
Jose F. Quilez del Moral, Alvaro Perez, Maria del Mar Herrador, Alejandro F. Barrero
JOURNAL OF NATURAL PRODUCTS
(2019)
Article
Biochemistry & Molecular Biology
Alberto Galisteo Pretel, Helena Perez del Pulgar, Estela Guerrero de Leon, Jose Luis Lopez-Perez, A. Sonia Olmeda, Azucena Gonzalez-Coloma, Alejandro F. Barrero, Jose Francisco Quilez del Moral
Article
Plant Sciences
Jose Francisco Quilez del Moral, Alvaro Perez, Alejandro F. Barrero
PHYTOCHEMISTRY REVIEWS
(2020)
Article
Chemistry, Multidisciplinary
Fabio M. F. Santos, Zoe Dominguez, Joao P. L. Fernandes, Catia Parente Carvalho, Daniel Collado, Ezequiel Perez-Inestrosa, Maria V. Pinto, Adelaide Fernandes, Jesus F. Arteaga, Uwe Pischel, Pedro M. P. Gois
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
Jose A. Gonzalez-Delgado, Miguel A. Romero, Francisco Bosca, Jesus F. Arteaga, Uwe Pischel
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Inorganic & Nuclear
Antonio A. Garcia-Valdivia, Andoni Zabala-Lekuona, Ainhoa Goni-Cardenas, Belen Fernandez, Jose A. Garcia, Jose F. Quilez del Moral, Javier Cepeda, Antonio Rodriguez-Dieguez
INORGANICA CHIMICA ACTA
(2020)
Article
Chemistry, Organic
Jose F. Quilez del Moral, Cristina Ruiz Martinez, Helena Perez del Pulgar, Juan Eduardo Martin Gonzalez, Ignacio Fernandez, Jose Luis Lopez-Perez, Alejandro Fernandez-Arteaga, Alejandro F. Barrero
Summary: The study demonstrates that water can be used as a solvent for the biomimetic-like synthesis of cannabinoids, with analysis of additives and reaction modes providing theoretical support. Similar reactions conducted in organic media using catalysts revealed a unique reaction process. Computational studies provided insights into the mechanism and energetics of the process.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Alberto Galisteo, Fatin Jannus, Amalia Garcia-Garcia, Houssam Aheget, Sara Rojas, Jose A. Lupianez, Antonio Rodriguez-Dieguez, Fernando J. Reyes-Zurita, Jose F. Quilez del Moral
Summary: A variety of diclofenac N-derivatives were synthesized and tested for their anti-cancer and anti-inflammatory effects, showing significant inhibitory effects on cancer cell lines and inflammatory responses. These compounds have the potential to be effective therapeutic strategies against diseases such as cancer and inflammation.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Plant Sciences
Jose Francisco Quilez del Moral, Alvaro Perez, Maria Jose Segura Navarro, Alberto Galisteo, Azucena Gonzalez-Coloma, Maria Fe Andres, Alejandro E. Barrero
Summary: Cardenolide-free extracts from Digitalis obscura exhibited significant antifeedant effects against aphids, with the activity correlated to their phenylethanoid content. The isolation of rengyolone and hallerone from D. obscura was achieved, with their antifeedant and nematicidal activities reported for the first time. This study provides new insights into the bioactivity of phenylethanoids from D. obscura.
Article
Chemistry, Multidisciplinary
Antonio M. Borrero-Lopez, David B. Guzman, Jose Antonio Gonzalez-Delgado, Jesus F. Arteaga, Concepcion Valencia, Uwe Pischel, Jose M. Franco
Summary: The new photocured bioadhesive, using o-nitrobenzyl-protected precursor as a phototrigger for the release of diamine cadaverine, demonstrates faster curing with UV light and superior adhesion performance, reaching lap shear strength values of up to 4600 kPa. Characterization with FTIR spectroscopy reveals a well-balanced urethane/urea composition and in-depth chemical analysis, showing the direct impact on adhesion properties. Additionally, the material bonds a variety of surfaces and has approximately the same viscoelastic properties as a result of the favored fast formation of urea bonds.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Analytical
Amalia Garcia-Garcia, Victor Toral, Jose F. Quilez del Moral, Alberto Galisteo Pretel, Diego P. Morales, Alfonso Salinas-Castillo, Javier Cepeda, Duane Choquesillo-Lazarte, Marco Bobinger, Jose F. Salmeron, Almudena Rivadeneyra, Antonio Rodriguez-Dieguez
Summary: In this study, a novel coordination polymer (CP) based on perylene-3,4,9,10-tetracarboxylate (pery) linkers and sodium metal ions was synthesized. By modifying the properties of the metal ions, we confirmed their role in the functionalization of the material and paved the way for the generation of sensitive and selective chemical sensors.
Article
Chemistry, Medicinal
Silvia Baldo, Patricia Antunes, Joao Falcao Felicidade, Fabio M. F. Santos, Jesus F. Arteaga, Fabio Fernandes, Uwe Pischel, Sandra N. Pinto, Pedro M. P. Gois
Summary: This study demonstrates that fluorescent boronic-acid derived salicylidenehydrazone complexes can be used as fluorescent linkers to monitor the delivery of proteasome inhibitor to cancer cells. The complexes were optimized for stability and sequestered by lipid droplets within cells, limiting hydrolysis and drug release. Conjugation with a cell-penetrating peptide improved cytoplasmic availability and potency against cancer cells.
ACS MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Organic
David Guzman Rios, Miguel A. Romero, Jose A. Gonzalez-Delgado, Jesus F. Arteaga, Uwe Pischel
Summary: The [Ru(bpy)2(Nor)2]2+ complex is an efficient catalyst for the aldol reaction of acetone with activated benzaldehydes in a buffered aqueous solution. The role of the metal as an activator for nornicotine organocatalyst ligands enhances catalytic activity by about 4.5 times compared to free nornicotine. The study provides insights into the synergistic effect of organic catalysts and metals.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Alvaro Perez, Jose F. Quilez del Moral, Alberto Galisteo, Juan M. Amaro, Alejandro F. Barrero
Summary: The antibiotic platensymicyn, which can be used to treat infections caused by multidrug-resistant bacteria, was successfully synthesized using a biomimetic approach. The starting materials used in the synthesis, ent-kaurenoic acid and grandiflorenic acid, can be obtained in large quantities from their natural sources. The key steps in the synthesis include long-distance functionalization of ent-kaurenoic acid at position C11 and an efficient protocol for degrading the A-ring of the diterpene framework.