High-pressure selectivity studies--a simple route to a homochiral wistarin precursor.
The cycloaddition of spirobutenolide 3 to the homochiral cyclopentadiene 1 at 6.5 kbar leads exclusively to cycloadduct 5. Subsequent Diels-Alder or Michael additions again favour the cyclohexenone double bond; this perfect chemo- regio- and face selectivity was employed for a short and efficient approach to the wistarin framework.
Knappwost-Gieseke
Costanze
C
Humanchemie GmbH, Hinter dem Kruge 5 31061 Alfeld, Germany.
Nerenz
Frank
F
Wartchow
Rudolf
R
Winterfeldt
Ekkehard
E