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High-pressure selectivity studies--a simple route to a homochiral wistarin precursor |
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| Authors: | Knappwost-Gieseke Costanze Nerenz Frank Wartchow Rudolf Winterfeldt Ekkehard |
| Institution: | Humanchemie GmbH, Hinter dem Kruge 5 31061 Alfeld, Germany. |
| Abstract: | 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. |
| Keywords: | cycloaddition diastereoselectivity Diels–Alder reactions high‐pressure chemistry |
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