scholarly journals Preparation of the Key Dolutegravir Intermediate via MgBr2-Promoted Cyclization

Molecules ◽  
2021 ◽  
Vol 26 (10) ◽  
pp. 2850
Author(s):  
Jiahui Kong ◽  
Haijian Xia ◽  
Renbao He ◽  
Hao Chen ◽  
Yongping Yu
Keyword(s):  
Intramolecular Cyclization ◽  
Oxalyl Chloride ◽  
Dimethyl Acetal ◽  
Selective Hydrolysis ◽  
Excellent Yield ◽  
Novel Approach ◽  
Hydrolysis Of ◽  
Subsequent Substitution

A novel approach for synthesizing the key dolutegravir intermediate is described via MgBr2-promoted intramolecular cyclization. Condensation of commercially available methyl oxalyl chloride and ethyl 3-(N,N-dimethylamino)acrylate afforded the vinylogous amide in an excellent yield. Subsequent substitution by aminoacetaldehyde dimethyl acetal and methyl bromoacetate gave rise to the expected precursor for cyclization, which was promoted by MgBr2 to highly selectively convert into pyridinone diester. The key dolutegravir intermediate was finally prepared by the selective hydrolysis of the corresponding diester via LiOH.

Selective hydrolysis of flavonoid glycosides by Curvularia lunata

2014 ◽  
Vol 11 (6) ◽  
pp. 684-689 ◽  
Author(s):  
Jing-Yuan LIU ◽  
He-Shui YU ◽  
Bing FENG ◽  
Li-Ping KANG ◽  
Xu PANG ◽  
...  
Keyword(s):  
Flavonoid Glycosides ◽  
Curvularia Lunata ◽  
Selective Hydrolysis ◽  
Hydrolysis Of

Bi(III) as New Catalyst for the Selective Hydrolysis of Esters

1997 ◽  
Vol 38 (17) ◽  
pp. 2981-2984 ◽  
Author(s):  
Véronique Le Boisselier ◽  
Michèle Postel ◽  
Elisabet Duñach
Keyword(s):  
Selective Hydrolysis ◽  
Hydrolysis Of Esters ◽  
Hydrolysis Of

Selective hydrolysis of perfluorochloromethylsulfenyl chlorides

1983 ◽  
Vol 23 (5) ◽  
pp. 471 ◽  
Author(s):  
A. Haas ◽  
W. Wanzke ◽  
N. Welcman
Keyword(s):  
Selective Hydrolysis ◽  
Hydrolysis Of

ChemInform Abstract: Highly α-Selective Hydrolysis of α,β-Epoxyalcohols Using Tetrabutylammonium Fluoride.

ChemInform ◽  
2010 ◽  
Vol 42 (2) ◽  
pp. no-no
Author(s):  
Purba Mukerjee ◽  
Mohammed Abid ◽  
Frank C. Schroeder
Keyword(s):  
Selective Hydrolysis ◽  
Tetrabutylammonium Fluoride ◽  
Hydrolysis Of

Sequence Selective Hydrolysis of Linear DNA Using Conjugates of Zr(IV) Complexes and Peptide Nucleic Acids

2003 ◽  
Vol 42 (26) ◽  
pp. 8618-8620 ◽  
Author(s):  
Felix H. Zelder ◽  
Andriy A. Mokhir ◽  
Roland Krämer
Keyword(s):  
Nucleic Acids ◽  
Peptide Nucleic Acids ◽  
Selective Hydrolysis ◽  
Linear Dna ◽  
Hydrolysis Of

Synthesis of Multi-Substituted Bicycloalkyl Boronates: An Intramolecular Coupling Approach to Alkyl Bioisosteres

2021 ◽  
Author(s):  
Yangyang Yang ◽  
Jet Tsien ◽  
Jonathan Hughes ◽  
Byron Peters ◽  
Rohan Merchant ◽  
...  
Keyword(s):  
Intramolecular Cyclization ◽  
Material Chemistry ◽  
Novel Approach ◽  
Coupling Approach ◽  
New Type ◽  
Strain Release ◽  
Synthetic Studies ◽  
Bicyclic Molecules

<p>Bicyclic hydrocarbons, bicyclo[1.1.1]pentanes (BCPs) in particular, play an emerging role as saturated bioisosteres in pharmaceutical, agrochemical, and material chemistry. Taking advantage of strain release strategies, prior synthetic studies have featured the synthesis of bridgehead-substituted (C1, C3) BCPs from [1.1.1]propellane. This work describes a novel approach to accessing multi-substituted BCPs via a new type of intramolecular cyclization. In addition to the C1, C3-disubstituted BCPs, this method also enables the construction of yet underexplored tri-substituted (C1, C2 and C3) BCPs from readily accessible cyclobutanones. The broad generality of this cyclization is examined through synthesis of a variety of caged bicyclic molecules, ranging from [1.1.1] to [3.2.1] scaffolds. The modularity afforded by the pendant bridgehead Bpin resulted from the cyclization is demonstrated via several downstream functionalizations, highlighting the ability of this approach for programmed and divergent synthesis of multi-substituted bicyclic hydrocarbons.<br></p>

Polyoxometalates as sialidase mimics: selective and non-destructive removal of sialic acid from a glycoprotein promoted by phosphotungstic acid

2017 ◽  
Vol 53 (76) ◽  
pp. 10600-10603 ◽  
Author(s):  
Laura Sofia Van Rompuy ◽  
Tatjana N. Parac-Vogt
Keyword(s):  
Sialic Acid ◽  
Phosphotungstic Acid ◽  
Glycosidic Bond ◽  
Selective Hydrolysis ◽  
Fetuin A ◽  
Keggin Type ◽  
Terminal Sialic Acid ◽  
Non Destructive ◽  
Hydrolysis Of

The selective hydrolysis of the glycosidic bond between the terminal sialic acid and the penultimate sugar has been achieved in the alpha-2-HS-glycoprotein (Fetuin-A) in the presence of H3PW12O40, a Keggin type polyoxometalate.

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