Concise, asymmetric syntheses of prostaglandin PGF 2α and latanoprost
| Autor: | Coulthard, Graeme |
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| Rok vydání: | 2012 |
| Předmět: | |
| Druh dokumentu: | Electronic Thesis or Dissertation |
| Popis: | 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. |
| Databáze: | Networked Digital Library of Theses & Dissertations |
| Externí odkaz: |
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