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Title: Towards the total synthesis of Daphniyunnine B
Author: Ward, John William
ISNI:       0000 0004 2698 0967
Awarding Body: University of Manchester
Current Institution: University of Manchester
Date of Award: 2010
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This thesis describes the development of a series of synthetic routes towards the first synthesis of Daphniyunnine B, a Daphniphyllum alkaloid, utilising novel reactions and cascades. Studies began with an envisaged enantioselective Michael cascade reaction, which alternatively gave rise to a novel, efficient Michael-aldol cascade reaction affording perhydroindole structures in moderate to excellent diastereoselectivity. The enantioselective synthesis of the methyl-substituted core of Daphniyunnine B was achieved via an initial highly enantioselective organocatalytic Michael addition followed by a stereoselective organocatalytic intramolecular Michael addition.The stereocontrolled synthesis of the AC bicyclic core of (±) Daphniyunnine B was achieved via a quaternisation cyclisation approach.The stereo controlled synthesis of the ACD tricyclic core of (±) Daphniyunnine B was achieved via an intramolecular Diels-Alder fragmentation reaction. Preliminary studies of an enantioselective variant are encouraging.
Supervisor: Procter, David Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available