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  4. Application of the novel tandem process Diels-Alder reaction/Ireland-Claisen rearrangement to the synthesis of rac-juvabione and rac-epijuvabione
 
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Application of the novel tandem process Diels-Alder reaction/Ireland-Claisen rearrangement to the synthesis of rac-juvabione and rac-epijuvabione

Auteur(s)
Soldermann, Nicolas
Velker, Joerg
Vallat, Olivier
Stoeckli-Evans, Helen 
Institut de physique 
Neier, Reinhard 
Institut de chimie 
Date de parution
2000-1-12
In
Helvetica Chimica Acta
Vol.
9
No
83
De la page
2266
A la page
2276
Mots-clés
  • JUVENILE-HORMONE ACTIVITY
  • STEREOCONTROLLED SYNTHESIS
  • 3-AZA-COPE
  • REARRANGEMENT
  • STEREOCHEMICAL CONTROL
  • ACRYLOYL CHLORIDE
  • GRIGNARD-REAGENTS
  • ORGANIC-SYNTHESIS
  • THIOCYANIC ACID
  • ACYL CHLORIDES
  • (+)-JUVABIONE
  • JUVENILE-HORMONE ACTI...

  • STEREOCONTROLLED SYNT...

  • 3-AZA-COPE

  • REARRANGEMENT

  • STEREOCHEMICAL CONTRO...

  • ACRYLOYL CHLORIDE

  • GRIGNARD-REAGENTS

  • ORGANIC-SYNTHESIS

  • THIOCYANIC ACID

  • ACYL CHLORIDES

  • (+)-JUVABIONE

Résumé
The novel tandem process Diels-Alder reaction/Ireland-Claisen rearrangement shows a high diastereoselectivity for the Ireland-Claisen rearrangement starting from the endo-product of the Diels-Alder reaction. Based on this mechanistic knowledge, the novel tandem process could be applied to the synthesis of rac-juvabione.
Identifiants
https://libra.unine.ch/handle/123456789/6411
Type de publication
journal article
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