Use this URL to cite or link to this record in EThOS: https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.351339
Title: The total synthesis of (+ or -)-ancistrofuran
Author: Cottrell, Ian Frank
ISNI:       0000 0001 3390 1612
Awarding Body: University of Southampton
Current Institution: University of Southampton
Date of Award: 1984
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Abstract:
A route to (+/-)-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 (+/-)-ancistrofuran from a trans-fused hemiacetal by reaction with 3-furyllithium and subsequent dehydration has been developed.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID: uk.bl.ethos.351339  DOI: Not available
Keywords: Termite defence secretions
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