160481-43-6Relevant academic research and scientific papers
Synthesis method of 1-iodo-alkyne compound
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Paragraph 0096-0099, (2021/01/24)
The invention discloses a synthetic method of a 1-iodo-alkyne compound. The preparation method comprises the following steps: in an aerobic environment, mixing terminal alkyne, soluble inorganic iodized salt, sodium phenylsulfinate or a derivative thereof
SYNTHESIS OF DISORAZOLES AND ANALOGS THEREOF AS POTENT ANTICANCER AGENTS
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Page/Page column 89; 103, (2019/01/11)
In one aspect, the present disclosure provides disorazole analogs of the formula: Formula (I) wherein the variables are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein. Additionally, drug conjugates with cell targeting moieties of the compounds are also provided.
Total Syntheses of Disorazoles A1 and B1 and Full Structural Elucidation of Disorazole B1
Nicolaou,Bellavance, Gabriel,Buchman, Marek,Pulukuri, Kiran Kumar
supporting information, p. 15636 - 15639 (2017/11/14)
Described herein are the first total syntheses of naturally occurring antitumor agents disorazoles A1 and B1 and the full structural assignment of the latter. The syntheses were achieved through convergent strategies employing enantioselective constructions of the required building blocks, including a novel Sharpless epoxidation/enzymatic kinetic resolution of stannane-containing substrates that led selectively to both enantiomeric forms of an epoxy vinyl stannane, and a series of coupling reactions, including a Wittig reaction, a Suzuki coupling, a Stille coupling, a Yamaguchi esterification and a Yamaguchi macrolactonization.
Method for synthesizing 1-iodo-alkyne in high-selectivity manner
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Paragraph 0056-0058, (2017/08/30)
The invention belongs to the technical field of synthetic chemistry and particularly relates to a method for synthesizing 1-iodo-alkyne in a high-selectivity manner. The method is mild in reaction condition, controllable in reaction product, single in pro
Intramolecular palladium-catalyzed alkene carboalkynylation
Nicolai, Stefano,Swallow, Peter,Waser, Jerome
supporting information, p. 5959 - 5964 (2015/08/03)
Abstract Carbocycles are essential building blocks for the synthesis of natural and synthetic bioactive compounds. Herein, we report the first example of palladium-catalyzed intramolecular carboalkynylation of non-activated olefins. Using activated carbon
Room-Temperature Decarboxylative Alkynylation of Carboxylic Acids Using Photoredox Catalysis and EBX Reagents
Le Vaillant, Franck,Courant, Thibaut,Waser, Jerome
supporting information, p. 11200 - 11204 (2016/07/06)
Alkynes are used as building blocks in synthetic and medicinal chemistry, chemical biology, and materials science. Therefore, efficient methods for their synthesis are the subject of intensive research. Herein, we report the direct synthesis of alkynes fr
Gold-catalyzed regioselective synthesis of 2- and 3-alkynyl furans
Li, Yifan,Brand, Jonathan P.,Waser, Jerome
supporting information, p. 6743 - 6747 (2013/07/26)
Chemical Matching: C2- or C3-alkynylated furans were selectively synthesized by using gold catalysis. Direct C-H alkynylation of furans was achieved with C2 selectivity, and a domino cyclization/alkynylation process starting from allenes gave C3-alkynylat
Catalytic electrophilic halogenation of silyl-protected and terminal alkynes: Trapping gold(I) acetylides vs. a Bronsted acid-promoted reaction
Starkov, Pavel,Rota, Filippo,D'Oyley, Jarryl M.,Sheppard, Tom D.
supporting information, p. 3217 - 3224 (2013/01/15)
In the presence of a cationic gold(I) catalyst and N-halosuccinimide, both trimethylsilyl-protected and terminal alkynes are converted into alkynyl halides. Further experiments showed that silyl-protected alkynes undergo electrophilic iodination and bromination under Bronsted acid catalysis, whilst terminal alkynes require a cationic gold catalyst. The former reactions probably proceed via activation of the electrophile, whilst the latter reactions proceed via a gold(I) acetylide intermediate. Gold-catalysed halogenation was further combined with gold-catalysed hydration and subsequent annulation to provide convenient routes to iodomethyl ketones and five-membered aromatic heterocycles. Copyright
A palladium-catalyzed aminoalkynylation strategy towards bicyclic heterocycles: Synthesis of (±)-trachelanthamidine
Nicolai, Stefano,Piemontesi, Cyril,Waser, Jerome
supporting information; experimental part, p. 4680 - 4683 (2011/06/23)
Sweet cyclizations: The synthesis of pyrrolizidines and indolizidines has been achieved. Olefins were subjected to an intramolecular palladium-catalyzed aminoalkynylation with the hypervalent iodine reagent TIPS-EBX. After removal of the protecting group, a two-step cyclization sequence and subsequent reduction led to the natural product (±)-trachelanthamidine (see scheme; TIPS-EBX=triisopropylsilyl ethynylbenziodoxolone).
Pd(0)-catalyzed oxy- and aminoalkynylation of olefins for the synthesis of tetrahydrofurans and pyrrolidines
Nicolai, Stefano,Waser, Jerome
supporting information; experimental part, p. 6324 - 6327 (2012/01/13)
The first Pd(0)-catalyzed intramolecular oxy- and aminoalkynylation of nonactivated olefins is reported. The reaction gives access to important tetrahydrofuran and pyrrolidine heterocycles with high diastereoselectivity. The unique synthetic potential of acetylenes is further exploited to access key building blocks for the synthesis of bioactive natural products.
