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Title: Concise, asymmetric syntheses of prostaglandin PGF 2α and latanoprost
Author: Coulthard, Graeme
Awarding Body: University of Bristol
Current Institution: University of Bristol
Date of Award: 2012
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This thesis describes concise asymmetric syntheses of prostaglandin PGF2u (7 steps) and the anti glaucoma drug latanoprost. A one-pot proline-catalysed aldol reaction of succinaldehyde and subsequent intramolecular aldol reaction and dehydration reaction gave a bicyclic enal in excellent enantioselectivity on multi-gram scale. This bicyclic enal was converted to PGF2u in five further steps. The lower side-chain was introduced by a conjugate addition reaction and the enolate trapped as a silyl enol ether. The C-II alcohol was installed by a reductive ozonolysis of the silyl enol ether. Both reactions proceeded with excellent selectivity which allowed a gram scale synthesis of PGF 2u to be completed by deprotection and a Wittig reaction.
Supervisor: Aggarwal, V. K. Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available