10313-60-7Relevant articles and documents
Practical Decagram-Scale Synthesis of a Lamellarin Analogue and Deprotection of Lamellarin Isopropyl Ethers
Klintworth, Robin,de Koning, Charles B.,Michael, Joseph P.
, p. 3860 - 3871 (2020)
Modular syntheses of naturally occurring lamellarin ε (5) and the synthetic analogue dehydrolamellarin J (6), both of them promising lead candidates for anticancer activity, were accomplished in high overall yields. Key steps in these routes are a late-st
Oxidative route to pyrroloisoquinoline-2,3-dione
Kadam, Hari K.,Tilve, Santosh G.
, p. 184 - 190 (2018)
We herein report an efficient constructive method for synthesis of structurally important Pyrroloisoquinoline-2,3-dione from dihydroisoquinoline through oxidative cyclisation. Process is optimised to give best efficiency at gram scale and laborious purification techniques such as column chromatography or recrystallisation were avoided in all steps further featuring uniqueness of this method as compared to the available literature.
Structure-based optimization of non-peptidic Cathepsin D inhibitors
Gr?dler, Ulrich,Czodrowski, Paul,Tsaklakidis, Christos,Klein, Markus,Werkmann, Daniela,Lindemann, Sven,Maskos, Klaus,Leuthner, Birgitta
, p. 4141 - 4150 (2014)
We discovered a novel series of non-peptidic acylguanidine inhibitors of Cathepsin D as target for osteoarthritis. The initial HTS-hits were optimized by structure-based design using CatD X-ray structures resulting in single digit nanomolar potency in the
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Fischer,Kulka,Hibbert
, p. 598,601 (1944)
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Lewis Acid and Fluoroalcohol Mediated Nucleophilic Addition to the C2 Position of Indoles
Morimoto, Naoki,Morioku, Kumika,Suzuki, Hideyuki,Takeuchi, Yasuo,Nishina, Yuta
, p. 2020 - 2023 (2016)
Indole readily undergoes nucleophilic substitution at the C3 site, and many indole derivatives have been functionalized using this property. Indole also forms indolium, which allows electrophilic addition in acidic conditions, but current examples have been limited to intramolecular reactions. C2 site-selective nucleophilic addition to indole derivatives using fluoroalcohol and a Lewis acid was developed.
A Simple and Efficient Synthesis of Fused Benzo[ b ]thiophene Derivatives
Ulyankin, Evgeny B.,Kostyuchenko, Anastasia S.,Chernenko, Sergey A.,Bystrushkin, Mikhail O.,Samsonenko, Anna L.,Shatsauskas, Anton L.,Fisyuk, Alexander S.
, p. 2422 - 2434 (2021/04/21)
A new approach to the synthesis of fused benzothiophene derivatives was developed based on iodine-promoted photocyclization of 4,5-diaryl-substituted thiophenes obtained in three steps from commercially available compounds. Comparative analysis showed that photochemical cyclization is a more efficient method for the preparation of fused benzo[ b ]thiophene derivatives, compared to oxidative coupling of 4,5-diaryl-substituted thiophenes in the presence of iron(III) chloride and palladium-catalyzed intramolecular arylation. This new approach provides an efficient synthesis of functionally substituted naphtho[2,1- b:3,4- b ′]dithiophenes, phenanthro[9,10- b ]thiophenes, benzo[1,2- b:3,4- b ′:6,5- b ′′]trithiophenes, as well as new fused heterocycles containing a pyridine ring and/or a carbazole moiety.
Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C-H Functionalization Cascades
Bower, John F.,Caiger, Lewis,García-Cárceles, Javier,Hazelden, Ian R.,Jones, Benjamin T.,Langer, Thomas,Lewis, Richard J.
supporting information, p. 15593 - 15598 (2021/10/12)
Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses N-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation in advance of C-H palladation of the aromatic component. The chemistry is showcased in the first total synthesis of the complex alkaloid (+)-pileamartine A, which has resulted in the reassignment of its absolute stereochemistry.
Demethylative Lactonization Provides a Shortcut to High-Yielding Syntheses of Lamellarins
De Koning, Charles B.,Klintworth, Robin,Michael, Joseph P.
, (2020/01/31)
Modular gram-scale syntheses of the trimethyl ethers of lamellarins G (6) and D (7) were achieved from readily accessible precursors in the highest overall yields reported to date (6, six steps, 82%; 7, seven steps, 86%). A novel demethylative lactonizati
