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Title: Synthetic studies on natural products
Author: Wang, Pu
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 1995
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This thesis consists of three relative independent projects all of which concentrate on the syntheses of biologically active natural products. In the first project, a convenience route for synthesis of [8-3H]-berberine sulfate has been established and two routes for preparation of 14C labelled berberine are explored. A series of compounds containing a methylenedioxyphenyl functionality have been synthesised for using as antigens in immunological studies. The second project concerns development of chemistry directed towards the stereocontrolled synthesis of Baogongteng A, a novel 2,6-disubstituted tropane alkaloid which is a powerful M-cholinergic agonist used in the treatment of glaucoma. By exploiting 4-hydroxy-L-proline as the chiral synthon, useful methods such as preparation of 2-formyl 4-hydroxy-L-proline derivatives, and the stereoselective bromination of the C-3 of 4-hydroxy-L-proline derivatives, have been established. About forty new organic compounds have been synthesised and identified. The final project concerns exploration of new routes for the syntheses of biotin biosynthetic precursors and their fluorined analogues which are types of compounds potentially valuable in agricultural chemistry. This work has led to the development of methods of wide application, such as the preparation of highly purified N-Boc-L-alaninal, which should prove to be of use in future studies in this and related fields.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available