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Title: The synthesis and biological evaluation of natural and unnatural cyclopentenone prostanoids
Author: Snape, Timothy J.
ISNI:       0000 0001 3469 6016
Awarding Body: University of Liverpool
Current Institution: University of Liverpool
Date of Award: 2003
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Research into the synthesis and biological properties of the cyclopentenone prostaglandins has become the focus of many research groups over the past few years. The ability for cyclopentenone prostaglandins, for example prostaglandin AI. to reduce virus yields and inflammation, both in vitro and in vivo, and to act as anticancer agents in vitro has made them important biological targets. o .••",~COOH OH prostaglandin Al In view of this, a great deal of work is currently being undertaken towards the preparation of cyclopentenone prostaglandin analogues, in the hope of harnessing the innate biological activity of this system. Part of the ongoing research into the cyclopentenone prostaglandins is the work currently being undertaken at The University of Liverpool, and this Ph.D. thesis is part of the contribution made by the Roberts' group. This thesis begins with an introductory section, Chapter 1, outlining the background and biological properties of the natural prostaglandins, along with examples of their chemical syntheses and some of the work carried out on other, related cyclopentenone-based natural products. Chapter 2 goes on to elaborate upon the biological results obtained during the course of this Ph.D., the synthesis of various prostaglandin analogues and the discussion of these results. The latter part of Chapter 2 describes the synthesis and ultimately the revision of stereochemistry of a natural product isolated from ascomycete strain A23-98. It has been shown that a-iodo-cyclopentenone 160, generated in 7 steps from Dribose, can undergo a palladium-catalysed Stille reaction, followed by deprotection of the masked diol, to reveal the natural product syn-163. n-ribose steps i) (PhCNhPdCI2' CuI, AsPh] HO""' ..~ -~ HO,)JT~ syn-l63 (Z)-tributylpropenylstannane 160 ii) PPTS, MeOH Following the synthesis it was subsequently discovered that the geometry of the sidechain is cis, as shown in syn-163, and not trans as proposed by NMR studies and correlation to similar natural products. Finally, Chapter 3 describes the experimental details associated with the compounds prepared throughout this thesis, followed by a reference section giving relevant citations in the chemical literature.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available