Article
Chemistry, Organic
Thorsten Kinsinger, Uli Kazmaier
Summary: The Matteson homologation with vinyl nucleophiles is an efficient and versatile protocol for the synthesis of substituted chiral allyl alcohols in a highly stereoselective fashion, which can be further transformed into highly substituted unsaturated amino acids through zinc-chelated ester-enolate Claisen rearrangements with N-protected glycine. By varying the nucleophiles used in the Matteson homologations, control over both the stereogenic centers and the side-chain substitution pattern in the newly formed gamma,delta-unsaturated amino acids can be achieved.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zigmars Leitis, Guna Sakaine, Artis Kinens, Gints Smits
Summary: The total syntheses of three pyrrolo[1,4]benzodiazepine anticancer antibiotic family members, oxo-prothracarcin, oxotomaymycin, and boseongazepine B, were described. The syntheses utilized late-stage stereoselective olefination with modified Julia-Kocienski reagents, which could be conveniently prepared in two steps and reduced the number of linear steps. Detailed density functional theory (DFT) studies explained the stereochemical outcome of the key step.
Article
Chemistry, Multidisciplinary
Liang Gong, Qian Zhang, Demeng Xie, Wei Zhang, Shi-Yang Xu, Xia Zhang, Dawen Niu
Summary: A Ni-catalyzed Negishi coupling reaction can prepare 1,2-dialkyl enol ethers in a stereoconvergent fashion, using alpha-oxy-vinylsulfones as electrophiles. This reaction shows unique selectivity and general applicability, indicating potential for further use in cross-coupling reactions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Joshua A. Malone, Satish Chandra Philkhana, Jacob R. Stepherson, Fatimat O. Badmus, Frank R. Fronczek, Rendy Kartika
Summary: This article describes a new synthetic reaction that can generate all-carbon bisquaternary centers at the opposing side of alpha-carbons in cyclohexanone with four different substituents in a controlled manner.
Article
Chemistry, Organic
Md Nirshad Alam, Soumya Ranjan Dash, Anirban Mukherjee, Satish Pandole, Udaya Kiran Marelli, Kumar Vanka, Pradip Maity
Summary: The thermal O-to-C [1,3]-rearrangement of alpha-hydroxy acid derived enol ethers was achieved under mild conditions, facilitated by the 2-aminothiophenol protection of carboxylic acids. Experimental and theoretical evidence was presented for dissociative radical pair formation, captodative stability via aminothiophenol, and a unique solvent effect. Aminothiophenol was deprotected from rearrangement products and after derivatization to useful synthons.
Article
Chemistry, Organic
Kazutoshi Tomoya, Kazuaki Komiya, Daisuke Nakajima, Nariyoshi Umekubo, Satoshi Yokoshima
Summary: A total synthesis of kopsone was achieved by stereoselective preparation of an acyclic aldehyde with a protected hydroxylamine moiety through Ireland-Claisen rearrangement and intramolecular cycloaddition of an eight-membered cyclic nitrone, forming the 2-azabicyclo[3.3.1]nonane skeleton.
Article
Chemistry, Multidisciplinary
Maximilian Kaiser, Michael Steinacher, Florian Lukas, Peter Gaertner
Summary: A general protocol for the europium-catalyzed rearrangement of aryl-pentadienyl-ethers is described, where the mode of rearrangement and product formation is determined by the substituent para to the phenol. The reaction undergoes a [3,3] rearrangement to form a prochiral branched diene when the para-position is occupied, and a [5,5] rearrangement to form a linear conjugated diene when the para-position is free.
Article
Chemistry, Organic
Yuichiro Kawamoto, Fuka Karube, Toyoharu Kobayashi, Hisanaka Ito
Summary: Mollebenzylanols A and B, tyrosine phosphatase 1B inhibitors with highly oxygenated structures, were successfully synthesized in 13 and 11 steps, respectively. Both compounds were derived from a common allyl alcohol and different rearrangement reactions were used to obtain them.
Article
Chemistry, Organic
Hussein Abou-Hamdan, Regis Guillot, Cyrille Kouklovsky, Guillaume Vincent
Summary: This study presents the synthesis of an acyclic iso-secologanin aglycone analogue relevant to secoiridoids and monoterpene indole alkaloids. The synthesis involved regioselective allylic alkylation and anti-Markovnikov Wacker-type oxidation to obtain the final product, which could be further utilized in the synthesis of monoterpene indole alkaloids.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Zhi-Jie Niu, Lian-Hua Li, Xue-Song Li, Hong-Chao Liu, Wei-Yu Shi, Yong-Min Liang
Summary: A new transition-metal-free intermolecular Claisen rearrangement process has been developed to introduce allyl and allenyl groups into the alpha position of tertiary amides. This atom-economical process delivers alpha position-modified amides under mild conditions in moderate to good yields and showcases a broad substrate compatibility.
Article
Biochemistry & Molecular Biology
Song-Wei Jiang, Xiang Qi, Haowen Deng, Yuan Gao, Yinghui Yuan, Xiawen Dang, Bing Xu, Shitang Ma, Tian Xie, Xiang-Yang Ye, Zi Hui
Summary: Polyphenols such as resveratrol, honokiol and nordihydroguaiaretic acid, which are widely found in nature or synthesized compounds, exhibit interesting biological activities. In this study, 49 1,3-diaryl propane-based polyphenols were designed and synthesized, and their anti-proliferative activities against various cancer cell lines were evaluated. Two compounds, 2t and 3t, showed promising anti-tumor efficacy in COLO205 xenografted mice model.
BIOORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Wei-Jung Chiu, Jin-Yu Chen, Shih- Liu, Indrajeet J. Barve, Wan-Wen Huang, Chung-Ming Sun
Summary: A one-pot, two-step synthesis of isoquinoline-fused isoquinolines from alpha-amino acid esters and 2-alkynyl benzaldehydes is reported. The strategy involves an unconventional Pictet-Spengler reaction and subsequent gold-catalyzed intramolecular hydroamination. The scope of this strategy is further extended to prepare multisubstituted isoquinoline-fused isoquinolines.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Rui-Han Dai, Qi Wang, Zhi-Xiong Chen, Shi-Kai Tian
Summary: An unprecedented asymmetric aza-Claisen rearrangement was discovered to proceed without catalysts and additives, providing easy access to structurally diverse delta-chiral beta-diketones with high yields and excellent retention of enantiopurity. This protocol proved powerful for the construction of an all-carbon quaternary stereocenter with high enantiopurity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Narra Rajashekar Reddy, Shaik Gouse, Sudhagar Selvaraju, Sundarababu Baskaran
Summary: A facile domino strategy for the synthesis of biologically active cyclopent-2-enone core containing CA-4 analogues has been developed. The methodology involves a sequence of semipinacol rearrangement, iterative aldol condensation, and iso-Nazarov cyclization reactions. Enantioselective synthesis of S-hydroxy-cyclopent-2-enones using the Sharpless AD catalyst was also achieved. Biological studies showed better inhibitory activity against cell proliferation for (S)-enantiomers than (R)-enantiomers.
Article
Chemistry, Organic
Paola Marzullo, Alice Maiocchi, Giuseppe Paladino, Umberto Ciriello, Leonardo Lo Presti, Daniele Passarella
Summary: The paper presents an enantioselective total synthesis of Cannabidiol-C-4, a natural product found in Cannabis extracts. The synthesis involves the use of 3,5-dimetoxybenzaldehyde as a starting material and includes several key steps such as Corey-Bakshi-Shibata reduction, Claisen-Ireland rearrangement, and ring-closing metathesis. The synthesized compound was characterized spectroscopically and confirmed to be present in low amounts in the extracts.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Lucilla Favero, Paolo Crotti, Valeria Di Bussolo, Elio Napolitano
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Valeria Di Bussolo, Salvatore Princiotto, Elisa Martinelli, Vittorio Bordoni, Paolo Crotti
TETRAHEDRON LETTERS
(2016)
Article
Chemistry, Multidisciplinary
Cinzia Chiappe, Gian Carlo Demontis, Valeria Di Bussolo, Maria Jesus Rodriguez Douton, Francesco Rossella, Christian Silvio Pomelli, Stefania Sartini, Stefano Caporali
Article
Chemistry, Organic
Valeria Di Bussolo, Ileana Frau, Lucilla Favero, Vittorio Bordoni, Stefano Crotti, Gloria Uccello Barretta, Federica Balzano, Paolo Crotti
Article
Chemistry, Organic
Salvatore Princiotto, Valeria Di Bussolo, Vittorio Bordoni, Lucilla Favero, Stefano Crotti, Gloria Uccello Barretta, Federica Balzano, Paolo Crotti
Article
Chemistry, Organic
Francesco Berti, Andrea Menichetti, Valeria Di Bussolo, Lucilla Favero, Mauro Pineschi
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2018)
Article
Chemistry, Medicinal
Andrea Menichetti, Francesco Berti, Lorenzo Guazzelli, Lucilla Favero, Sebastiano Di Pietro, Gennaro Pescitelli, Mauro Pineschi
Article
Chemistry, Medicinal
Michela Vargiu, Lucilla Favero, Andrea Menichetti, Valeria Di Bussolo, Fabio Marchetti, Gennaro Pescitelli, Sebastiano Di Pietro, Mauro Pineschi
Article
Biochemistry & Molecular Biology
Felicia D'Andrea, Giulia Vagelli, Carlotta Granchi, Lorenzo Guazzelli, Tiziano Tuccinardi, Giulio Poli, Dalila Iacopini, Filippo Minutolo, Valeria Di Bussolo
Article
Chemistry, Organic
Valeria Di Bussolo, Salvatore Princiotto, Vittorio Bordoni, Elisa Martinelli, Lucilla Favero, Stefano Crotti, Gloria Uccello-Barretta, Federica Balzano, Mauro Pineschi, Paolo Crotti
Article
Biochemistry & Molecular Biology
Sebastiano Di Pietro, Dalila Iacopini, Aldo Moscardini, Ranieri Bizzarri, Mauro Pineschi, Valeria Di Bussolo, Giovanni Signore
Summary: This study introduces two new tris coumarin-dipicolinate europium (III) complexes, which can be tailored to be either mono or dual emitters and their properties tuned with simple chemical modifications. The research also reveals a rich chemical speciation in solution, which is studied in detail by paramagnetic NMR and emission spectroscopy.
Article
Chemistry, Multidisciplinary
Manuela Curcio, Alessandro Paoli, Giuseppe Cirillo, Sebastiano Di Pietro, Martina Forestiero, Francesca Giordano, Loredana Mauro, Diana Amantea, Valeria Di Bussolo, Fiore Pasquale Nicoletta, Francesca Iemma
Summary: This study successfully prepared new dual pH/redox-responsive nanoparticles with affinity for folate receptors, demonstrating potential applicability as a new drug vector in cancer therapy.
Article
Biochemistry & Molecular Biology
Lucilla Favero, Andrea Menichetti, Cosimo Boldrini, Lucrezia Margherita Comparini, Valeria Di Bussolo, Sebastiano Di Pietro, Mauro Pineschi
Summary: The study reveals the structural requirements and reaction conditions for regioselective nucleophilic addition reaction on alkyl aziridines using bis(pinacolate)diboron under copper catalysis. This is important for the preparation of functionalized beta-aminoboronates, which are key compounds in drug discovery.
Article
Chemistry, Organic
Lucrezia Margherita Comparini, Andrea Menichetti, Lucilla Favero, Sebastiano Di Pietro, Fabrizio Badalassi, Per Ryberg, Mauro Pineschi
Summary: The stereoselective reduction of a diastereoisomeric mixture of benzo[g]octahydroquinolinium ion was examined in detail. A diastereoselective borohydride reduction in combination with an efficient deacylative enzymatic resolution of its β-aminoester precursor are the key steps for a stereoselective installation of the three chiral centers present in the (3S,4aS,10aR)-eutomer of the medicinal drug quinagolide. The obtained data paves the way for an easy and practical attainment of chiral 3-substituted octahydrobenzo[g]quinolines that are privileged structures in medicinal chemistry.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
