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Synthetic organic approaches towards heterocyclic and acyclic peptidomimetics.

Walsh, Rodney Mark. (2005) Synthetic organic approaches towards heterocyclic and acyclic peptidomimetics. Doctoral thesis, University of Surrey (United Kingdom)..

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The activation of delta-valerolactam with triflic anhydride is studied in detail. Triflic anhydride activation initially produces the O-triflated lactam I, which rearranges, following the addition of base, to the N-triflated derivative II. Increasing temperatures favour this triflate group migration, but only when a base is present. On reaction with a suitable nucleophile, the lactam ring is opened resulting in an acyclic product. The N-triflated derivatives have been reacted with a range of nucleophiles to produce esters and amides, which are formally dipeptides of o-amino acids. In addition, a synthetic pathway to 1,3,4-oxadiazole based dipeptide mimetics has been worked out starting from commercially available Boc-protected amino acids IV. This synthetic route improves on a published method for producing these types of compound, both in simplicity and yield of final compound. This route has been successfully used to synthesise novel hydrazide intermediates V and 1,3,4-oxadiazole products VI.

Item Type: Thesis (Doctoral)
Divisions : Theses
Authors :
Walsh, Rodney Mark.
Date : 2005
Contributors :
Depositing User : EPrints Services
Date Deposited : 09 Nov 2017 12:15
Last Modified : 15 Mar 2018 18:58

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