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Title: Towards the total synthesis of lactonamycin
Author: Jacques, Sylvain Michel Matthieu Arthur
Awarding Body: Imperial College London
Current Institution: Imperial College London
Date of Award: 2011
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The natural product lactonamycin (1) was isolated in Japan by Matsomoto et al. Biological evaluation of lactonamycin (1) against Gram-positive bacteria such as Staphylococcus aureus showed significant levels of antimicrobial activity and it was especially active against clinically isolated-MRSA and - VRE. In addition to interesting biological properties, lactonamycin (1) possesses an intriguing molecular architecture (Figure 1). The novel, highly functionalized hexacyclic aglycone core, known as lactonamycinone (2) contains, in the western half, a highly-oxygenated fused perhydrofuranfuranone bicycle connected to a labile tertiary methoxy group, and in the eastern half, a naphtha[e]isoindole ring system. Adding to the structural complexity of lactonamycin (1), a 2,3,6- trideoxy sugar unit is connected to the core via a highly hindered tertiary glycosidic linkage. [Molecular structure diagrams appear here. To view, please open pdf attachment] Figure 1 - Structures of lactonamycin (1) and lactonamycinone (2). A key step in the current strategy is an electrodecarboxylation reaction to introduce the angular methoxy group. Various experiments towards this electrodecarboxylation reaction are described using simple model substrates. In particular, the synthesis of model system (3) and investigations towards ABCD tetracycle model system (4) are described alongside our efforts towards the synthesis of lactonamycin (1) (Figure 2). Finally, a new synthesis of known boronic ester 5 was investigated using the biomimetic resorcylate methodology developed in the group. [Molecular structure diagrams appear here. To view, please open pdf attachment] Figure 2 – Structures of carboxylic model system 3, ABCD tetracycle model system 4 and boronic ester 5.
Supervisor: Barrett, Anthony Sponsor: Engineering and Physical Sciences Research Council
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available