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Figure 1.5 Determination of the absolute configuration of muironolide A (1.11) using
chemical degradation.
Muironolide A (1.11) was saponified and then esterified with α-bromo-ketone 1.12 to
yield degradation fragment 1.13 (Figure 1.5). A set of standards with known configuration
was prepared starting from menthol-methyl methacrylate 1.14. These standards were
compared with the muironolide degradation product 1.13. Chiral LCMS was used to show
that the muironolide A (1.11) degradation product and synthetic standard 1.13 were identical,
assigning the (3S,4S,5R) configuration to the natural product (Figure 1.5).
Another example of how synthesis can assist structural elucidation efforts is the
imidazole alkaloid (–)-palau’amine (1.22). (–)-Palau’amine (1.22) is an alkaloid produced by
the marine sponge Stylotella agminata. It was isolated in 1993 27 and represents the pinnacle
of structural complexity in a family of imidazole containing natural products including (–)-
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