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List of Figures
Figure 1.1 Bioactive compounds of plants commonly used throughout human history. ......... 1
Figure 1.2 Inhibitors of the 20S proteasome salinosporamide A (1.5) and omuralide (1.6). ... 4
Figure 1.3 Salinosporamide A (1.5) mechanism of action. ...................................................... 4
Figure 1.4 Marine natural product identification at the nM scale............................................. 7
Figure 1.5 Determination of the absolute configuration of muironolide A (1.11) using
chemical degradation. ............................................................................................................... 8
Figure 1.6 Family of imidazole marine natural products. ......................................................... 9
Figure 1.7 Barans retrosynthesis of (±)-palau’amine (1.22). .................................................. 10
Figure 1.8 The antimitotic marine natural product (+)-spongistatin 1 (1.27). ........................ 11
Figure 1.9 A pharmacophore analogue (1.28) of (+)-spongistatin 1 (1.27). ........................... 12
Figure 1.10 A marine peptide with novel biological activity. ................................................ 13
Figure 2.1 The PI3K pathway. ................................................................................................ 16
Figure 2.2 The first selective SHIP1 activator marine natural product pelorol (2.1). ............ 18
Figure 2.3 Pelorol (2.1) analogue 2.2. .................................................................................... 19
Figure 2.4 Chemical and enzymatic oxidation of catechol and subsequent 1,6-addition. ...... 20
Figure 2.5 Analogue 2.3 without the catechol functionality. .................................................. 20
Figure 2.6 Natural products made by biomimetically-inspired syntheses. ............................. 22
Figure 2.7 Carbocation generation .......................................................................................... 22
Figure 2.8 Typical propagation and termination of a polyene cascade. ................................. 23
Figure 2.9 Water soluble prodrug analogues of 2.3. ............................................................... 26
Figure 2.10 Analogue 2.18...................................................................................................... 27
Figure 2.11 Water soluble analogue design. ........................................................................... 27
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