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Title: Approaches to the synthesis of nitensidine D and E /
Author: Al-Shuhaib, Zainab A. Mohammed Saleh
ISNI:       0000 0004 5363 8550
Awarding Body: Bangor University
Current Institution: Bangor University
Date of Award: 2014
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This thesis describes synthetic approaches directed towards the synthesis of the alkaloid natural products nitensidine D 213 and nitensidine E 214. The structurally less complex metabolite nitensidine D was prepared by the guanylation of commercially available geranylamine 254 whilst four synthetic approaches were attempted to prepare nitensidine E. Initially the 6-membered guanidines 225a-b, 256 and 257 were prepared via an iodocyclisation of the corresponding allylic 226a-b and homoallylic guanidines 255, whilst the guanidines 265a-b were prepared via a DMDO mediated epoxidation and acid catalysed cyclisation/ rearrangement reaction. Attempts to convert these to the desired metabolite were unsuccessful. FinallYl the cyclic guanidine 283 was prepared from the allylic acetate 281 via a palladium π-allyl cyclisation.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available