Application of the novel tandem process Diels-Alder reaction/Ireland-Claisen rearrangement to the synthesis of rac-juvabione and rac-epijuvabione
Author(s)
Soldermann, Nicolas
Velker, Joerg
Vallat, Olivier
Date issued
January 12, 2000
In
Helvetica Chimica Acta
Vol
9
No
83
From page
2266
To page
2276
Subjects
JUVENILE-HORMONE ACTIVITY STEREOCONTROLLED SYNTHESIS 3-AZA-COPE REARRANGEMENT STEREOCHEMICAL CONTROL ACRYLOYL CHLORIDE GRIGNARD-REAGENTS ORGANIC-SYNTHESIS THIOCYANIC ACID ACYL CHLORIDES (+)-JUVABIONE
Abstract
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.
Publication type
journal article