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product extracts. The last couple years has seen an increase to approximately 1000 new<br />

marine natural products <strong>with</strong> varying biological profiles being isolated per annum. 22<br />

This diversity in marine natural products may provide future drug c<strong>and</strong>idates.<br />

However, for any compound to achieve drug status 23 several major hurdles have to be<br />

overcome. It can be shown that synthetic organic chemistry plays a major role in each stage<br />

of development, from benchtop to bedside.<br />

1.2 Syn<strong>thesis</strong> as an Aid to Structure Elucidation<br />

The compounds first identified by marine natural product chemists were “low<br />

hanging fruit” that were present in large quantities in the source organisms, <strong>and</strong> were easily<br />

separable from other constituents in the extracts. This was a direct result of limited separation<br />

<strong>and</strong> spectroscopic technologies available in the early days of marine natural product<br />

discovery. As techniques for chemical identification became more sophisticated, smaller<br />

amounts of material could provide the necessary data needed to elucidate a chemical<br />

structure.<br />

A modern example is the macrolide phorboxazole A (1.9) that was isolated 24 from the<br />

marine sponge Phorbas sp. collected in Western Australia (Figure 1.4). Phorboxazole A (1.9)<br />

(95.1 mg) was isolated in the mid 1990’s at masses sufficient for characterization. A number<br />

of smaller peaks in the HPLC trace (0.78-3.0 mg) of the major metabolite (1.9) alluded to<br />

additional compounds. However, the NMR technology at the time was too insensitive for<br />

characterization of these minor components. Fifteen years would pass before phorbaside A 25<br />

(1.10) <strong>and</strong> muironolide A 26 (1.11) were characterized (Figure 1.4).<br />

6

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