scholarly journals Asymmetric Diels–Alder reaction of 3-(acyloxy)acryloyl oxazolidinones: optically active synthesis of a high-affinity ligand for potent HIV-1 protease inhibitors

RSC Advances ◽  
2019 ◽  
Vol 9 (71) ◽  
pp. 41755-41763
Author(s):  
Arun K. Ghosh ◽  
Alessandro Grillo ◽  
Satish Kovela ◽  
Margherita Brindisi
Keyword(s):  
Protease Inhibitors ◽  
Alder Reaction ◽  
Optically Active ◽  
Diels Alder ◽  
Active Synthesis ◽  
High Affinity ◽  
Affinity Ligand ◽  
Diels Alder Reaction ◽  
High Affinity Ligand ◽  
Hiv 1

Asymmetric Diels–Alder reaction of chiral 3-(acyloxy)acryloyl oxazolidinones and synthesis of hexahydro-4H-3,5-methanofuro[2,3-b]pyranol are described.

scholarly journals Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative

2013 ◽  
Vol 9 ◽  
pp. 655-663 ◽  
Author(s):  
Toshiki Tabuchi ◽  
Daisuke Urabe ◽  
Masayuki Inoue
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Optically Active ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Quaternary Carbons

The stereoselective Diels–Alder reaction between an optically active 1,4-dimethylcycloheptadiene and acrolein was effectively promoted by TBSOTf to produce a bicyclo[3.2.2]nonene derivative bearing two quaternary carbons. Seven additional transformations from the obtained bicycle delivered the C 2-symmetric bicyclo[3.3.2]decene derivative, a key intermediate in our synthetic study of ryanodine.

scholarly journals Synthesis of a Novel Bicyclic Scaffold Inspired by the Antifungal Natural Product Sordarin

2018 ◽  
Author(s):  
Yibiao Wu ◽  
Chris Dockendorff
Keyword(s):  
Carboxylic Acid ◽  
Natural Product ◽  
Elongation Factor ◽  
Alder Reaction ◽  
Diels Alder ◽  
High Affinity ◽  
Diels Alder Reaction ◽  
Elongation Factor 2 ◽  
Eukaryotic Elongation Factor 2 ◽  
Eukaryotic Elongation Factor

A simplified bicyclic scaffold inspired by the antifungal natural product sordarin was designed and synthesized which maintains the carboxylic acid/aldehyde (or nitrile) pharmacophore. A densely functionalized chiral cyclopentadiene was constructed in 8 steps and utilized in a Diels-Alder reaction with acrylonitrile. The resulting [2.2.1]cycloheptene was transformed into a scaffold possessing vicinal carboxylic acid and nitrile groups, with orientations predicted to provide high affinity for the fungal protein eukaryotic elongation factor 2 (eEF2).

Synthesis of Thioaldehydes Having Optically Active Alkoxy Moiety and Their Asymmetric Hetero Diels-Alder Reaction

Heterocycles ◽  
1993 ◽  
Vol 36 (7) ◽  
pp. 1601 ◽  
Author(s):  
Toru Koizumi ◽  
Tamiko Takahashi ◽  
Noriyuki Kurose ◽  
Motoo Shiro
Keyword(s):  
Alder Reaction ◽  
Optically Active ◽  
Diels Alder ◽  
Diels Alder Reaction
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