Cottrell, Ian Frank (1984) The total synthesis of (+ or -) - ancistrofuran. University of Southampton, Doctoral Thesis.
Abstract
A route to (t)-ancistrofuran has been investigated. A key step, the epoxidation of an exocyclic olefin was found to proceed in low yield. Two competing reactions, oxidation of the furan in the substrate and intramolecular hydroxyl group participation, have been identified. Conjugation of the furan with a ketone group was found to deactivate the aromatic ring towards m-chloroperbenzoic acid, allowing selective olefin epoxidation. This oxidation was stereoselective with the oxygen atom delivered exclusively to the more hindered face of the olefin. A mechanism involving participation of the ketone is suggested to account for this anomalous reaction. A stereoselective synthesis of the cis-fused ancistrofuran skeleton was achieved featuring this epoxidation as a key step. A short, new synthesis of (t)-ancistrofuran from a trans-fused hemiacetal by reaction with 3-furyllithium and subsequent dehydration has been developed.
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