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Synthetic Studies on the Pseudopterosins and trans-4-Methyl-L-Proline

Calabrese, Andrew A.; (2000) Synthetic Studies on the Pseudopterosins and trans-4-Methyl-L-Proline. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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The Pseudopterosin family of diterpene glycosides was isolated in 1986 from the Caribbean sea-plume Pseudopterogorgia elisabethea. Pseudopterosin E is one of the most potent anti-inflammatory agents currently know, being fifty times more active than indomethacin in preventing phorbol myristate acetate topically-induced inflammation in the mouse ear oedema model. In the first section of this thesis, an attempted synthetic strategy towards Pseudopterosin E is reported. Our initial retrosynthesis adopted an intramolecular Diels- Alder reaction (IMDA) to form the tricarbocyclic core of the natural product. It was envisaged that elaboration of the IMDA product would lead to a key intermediate in the Corey et al. synthesis of Pseudopterosin E. The remainder of our synthesis would be after Corey. Free trans-4-methyl-L-proline was first obtained from Worcester Pearmain apples in 1952. It is a constituent part of several natural products; Grisemelycin, Mycoplanecin A, and the Monamycins, all of which have potent biological activity profiles. In the second section of this thesis, several synthetic approaches to trans-4- methyl-L-proline are reported.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: Synthetic Studies on the Pseudopterosins and trans-4-Methyl-L-Proline
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Thesis digitised by ProQuest.
URI: https://discovery.ucl.ac.uk/id/eprint/10122688
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