A novel synthetic approach to steroids via intramolecular 1,3-dipolar cycloaddition. A highly stereocontrolled synthesis of testosterone

1990 ◽  
Vol 55 (15) ◽  
pp. 4497-4498 ◽  
Author(s):  
Masataka Ihara ◽  
Yuji Tokunaga ◽  
Keiichiro Fukumoto
Keyword(s):  
Dipolar Cycloaddition ◽  
Synthetic Approach ◽  
Stereocontrolled Synthesis

Preparation of enantiopure long chain threo-2-amino-3-hydroxyesters via chiral morpholinone-derived azomethine ylids

2006 ◽  
Vol 84 (10) ◽  
pp. 1448-1455 ◽  
Author(s):  
Victoria A Brome ◽  
Laurence M Harwood ◽  
Helen MI Osborn
Keyword(s):  
Amino Acid ◽  
Building Blocks ◽  
Dipolar Cycloaddition ◽  
Amino Acid Derivatives ◽  
Synthetic Approach ◽  
Alkyl Chains ◽  
Long Chain

The synthetic approach to threo-2-amino-3-hydroxyesters possessing long alkyl chains outlined herein centres on the generation of chiral azomethine ylids by reaction of (5R)-5-phenyl-morpholin-2-one, (R)-(1), with long chain aldehydes. In the presence of a second equivalent of aldehyde, the azomethine ylid can be trapped to afford a cycloadduct with three new stereodefined centres. Degradation of the cycloadduct allows entry to β-substituted-α-amino acid derivatives, which have potential as building blocks for sphingosine synthesis.Key words: sphingosine, morpholinone, chiral azomethine ylid, dipolar cycloaddition.

scholarly journals Synthesis and properties of new fused pyrrolo-1,10-phenanthroline type derivatives

2021 ◽  
pp. 57-57
Author(s):  
Cristina Al-Matarneh ◽  
Irina Rosca ◽  
Sergiu Shova ◽  
Ramona Danac
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Antimicrobial Activity ◽  
Spectroscopic Data ◽  
Molecular Structures ◽  
Dipolar Cycloaddition ◽  
Synthetic Approach ◽  
Good Activity ◽  
Substituted Acetylenes ◽  
Potential Antimicrobial Activity

New fused pyrrolo-phenanthroline type derivatives were synthesized, in two steps, from 1,10-phenanthroline and evaluated for antimicrobial activity and fluorescence properties. Our synthetic approach involved a 3+2 dipolar-cycloaddition of some selected N-substituted 1,10-phenanthrolin-1-ium ylides, (m)ethoxycarbonyl and cyano (1,2-di)substituted acetylenes and alkenes, respectively. The structures of compounds were supported by analytical and spectroscopic data. Molecular structures of four compounds have also been also determined by monocrystal XRD analyses. All synthesized compounds were then evaluated for their potential antimicrobial activity against Staphylococcus aureus ATCC25923, Escherichia coli ATCC25922 and Candida albicans ATCC10231. Two of the compounds demonstrated good activity against the above tested strains.

scholarly journals Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes

2017 ◽  
Vol 28 (10) ◽  
pp. 1423-1429 ◽  
Author(s):  
Ihssene Chabour ◽  
Luis M. Castelló ◽  
Juan Mancebo-Aracil ◽  
María Martín-Rodríguez ◽  
María de Gracia Retamosa ◽  
...  
Keyword(s):  
Hepatitis C Virus ◽  
Hepatitis C ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Synthetic Approach ◽  
Silver Catalyst ◽  
Virus Inhibitor ◽  
The Core

Theoretical and Synthetic Approach to Novel Spiroheterocycles Derived from Isatin Derivatives and L-Proline via 1,3-Dipolar Cycloaddition.

ChemInform ◽  
2003 ◽  
Vol 34 (20) ◽  
Author(s):  
R. T. Pardasani ◽  
P. Pardasani ◽  
V. Chaturvedi ◽  
S. K. Yadav ◽  
A. Saxena ◽  
...  
Keyword(s):  
Dipolar Cycloaddition ◽  
Synthetic Approach ◽  
Isatin Derivatives

A facile synthetic approach to novel spiro-oxindoles/acenaphthylen-1-ones containing benzo[1,4]thiazin-3-one ring via 1,3-dipolar cycloaddition

2011 ◽  
Vol 52 (41) ◽  
pp. 5301-5307 ◽  
Author(s):  
Neelakandan Vidhya Lakshmi ◽  
Rajendren Tamilisai ◽  
Paramasivan T. Perumal
Keyword(s):  
Dipolar Cycloaddition ◽  
Synthetic Approach

An Effective Approach to 1,2,3-Triazole-Containing 12-Vertex closo-Dodecaborates

2007 ◽  
Vol 72 (12) ◽  
pp. 1717-1724 ◽  
Author(s):  
Andrey A. Semioshkin ◽  
Sergey N. Osipov ◽  
Julia N. Grebenyuk ◽  
Evgueniya A. Nizhnik ◽  
Ivan A. Godovikov ◽  
...  
Keyword(s):  
Dipolar Cycloaddition ◽  
Synthetic Approach ◽  
Wide Range ◽  
Nucleophilic Cleavage

An efficient general synthetic approach giving a facile, rapid and inexpensive access to a wide range of novel 1,2,3-triazoles bearing closo-dodecaborate fragment has been developed. The method is based on the nucleophilic cleavage of oxonium dodecaborate with NaN3 or tertiary propargylamine and subsequent Huisgen 1,3-dipolar cycloaddition ("click" methodology) of the cleavage products and organic acetylenes or azides.

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