83665-55-8Relevant academic research and scientific papers
Synthesis of Nitrile-Bearing Quaternary Centers by an Equilibrium-Driven Transnitrilation and Anion-Relay Strategy
Alazet, Sébastien,West, Michael S.,Patel, Purvish,Rousseaux, Sophie A. L.
supporting information, p. 10300 - 10304 (2019/07/04)
The efficient preparation of nitrile-containing building blocks is of interest due to their utility as synthetic intermediates and their prevalence in pharmaceuticals. As a result, significant efforts have been made to develop methods to access these motifs which rely on safer and non-toxic sources of CN. Herein, we report that 2-methyl-2-phenylpropanenitrile is an efficient, non-toxic, electrophilic CN source for the synthesis of nitrile-bearing quaternary centers by a thermodynamic transnitrilation and anion-relay strategy. This one-pot process leads to nitrile products resulting from the gem-difunctionalization of alkyl lithium reagents.
Asymmetric Synthesis of Hispidanin A and Related Diterpenoids
Cao, Wei,Deng, Heping,Sun, Ying,Liu, Bo,Qin, Song
supporting information, p. 9120 - 9129 (2018/06/29)
We report on our accomplishment of the asymmetric synthesis of hispidanin A and its natural precursor, a labdane diterpenoid. In the first generation of synthesis, a semi-synthesis strategy was employed to construct a labdane-type diterpenoid, a natural precursor of hispidanin A, in which Barton's photolytic remote functionalization was employed as a key transformation. In addition, the totarane-type dienophile counterpart was derived from commercially available (?)-scalareol. In the second generation of synthesis, key elements included an iron-catalyzed radical cascade to access the labdane-type diene on the basis of hydrogen atom transfer, and an enantioselective cationic polyene cyclization furnished the totarane-type dienophile. Reaction optimization and mechanistic analysis of the radical cascade reaction was conducted. Furthermore, the [4+2] cycloaddition reaction was achieved in excellent yield and selectivity under thermal conditions, which has been rationalized by using DFT transition-state analysis and paved the way for final accomplishment of the total synthesis of hispidanin A.
Synthetic method of Myrioneuron faberi Hemsl. alkaloids
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Paragraph 0031; 0032, (2016/10/24)
Myrioneuron faberi Hemsl. alkaloids A and B and parts of derivatives thereof have a substantial inhibition effect on hepatic c viruses, and have lower cytotoxicity than a present hepatic c treatment drug telaprevir. Only 30mg of the Myrioneuron faberi Hemsl. alkaloid A and 2mg of the Myrioneuron faberi Hemsl. alkaloid B are separated from 30kg of Myrioneuron faberi Hemsl. plants, so the research difficulty of the physiological and pharmacological activities of the alkaloids is increased, and further researches and application of the above substances are obstructed. The invention provides a synthetic method of the Myrioneuron faberi Hemsl. alkaloids A and B to solve the disadvantage of obstruction of the further researches and application of the substances due to small obtaining amount of the Myrioneuron faberi Hemsl. alkaloids A and B. The method starts from the cheap and easily available raw material, realizes artificial synthesis of the Myrioneuron faberi Hemsl. alkaloids A and B for the first time, allows the Myrioneuron faberi Hemsl. alkaloids A and B to be continuously and massively synthesized, and provides good technical support for subsequent realization of large-scale production and structure activity relation researching of natural products.
Ligand-Enabled Meta-C-H Alkylation and Arylation Using a Modified Norbornene
Shen, Peng-Xiang,Wang, Xiao-Chen,Wang, Peng,Zhu, Ru-Yi,Yu, Jin-Quan
supporting information, p. 11574 - 11577 (2015/09/28)
2-Carbomethoxynorbornene is identified as a more effective transient mediator to promote a Pd(II)-catalyzed meta-C(sp2)-H alkylation of amides with various alkyl iodides as well as arylation with previously incompatible aryl iodides. The use of a tailor-made quinoline ligand is also crucial for this reaction to proceed.
Electrochemical synthesis and chemistry of chiral 1- cyanotetrahydroisoquinolines. An approach to the asymmetric syntheses of the alkaloid (-)-crispine A and its natural (+)-antipode
Louafi, Fadila,Moreau, Julie,Shahane, Saurabh,Golhen, Stephane,Roisnel, Thierry,Sinbandhit, Sourisak,Hurvois, Jean-Pierre
experimental part, p. 9720 - 9732 (2012/01/05)
The stereoselective convergent total syntheses of both enantiomers of the tetrahydroisoquinoline (THIQ) alkaloid crispine A are described. The THIQ precursors ( - )-6 (90:10 dr) and ( - )-11 (85:15 dr) were prepared from the alkylation - reduction sequenc
Palladium-catalyzed alkylation of ortho-C(sp2)-H bonds of benzylamide substrates with alkyl halides
Zhao, Yingsheng,Chen, Gong
experimental part, p. 4850 - 4853 (2011/11/06)
A highly efficient and generally applicable method has been developed to functionalize the ortho-C(sp2)-H bonds of picolinamide (PA)-protected benzylamine substrates with a broad range of β-H-containing alkyl halides. Sodium triflate has been identified as a critical promoter for this reaction system. The PA group can be easily installed and removed under mild conditions. This method provides a new strategy to prepare highly functionalized benzylamines for the synthesis of complex molecules.
Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan
Hsu,Fang
, p. 8573 - 8584 (2007/10/03)
By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) δ-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active δ-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.
Angiotensin converting enzyme inhibitors. 10. Aryl sulfonamide substituted N-[1-carboxy-3-phenylpropyl]-L-alanyl-L-proline derivatives as novel antihypertensives
Mencel,Regan,Barton,Menard,Bruno,Calvo,Kornberg,Schwab,neiss,Suh
, p. 1606 - 1615 (2007/10/02)
Compounds 1a-g consisting of enalaprilat covalently bonded to aryl sulfonamides, including several known thiazide diuretics, were synthesized and tested for ACE inhibitory and diuretic and overall antihypertensive effects. All compounds were potent ACE in
