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.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:664504 |
| Date | January 2014 |
| Creators | Al-Shuhaib, Zainab A. Mohammed Saleh |
| Publisher | Bangor University |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
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