Abstract
The absolute stereochemistry of the immunosuppressive pyrrole–imidazole alkaloid (−)-palau’amine from the marine sponge Stylotella aurantium is analyzed by CD spectroscopy. With the help of a series of model compounds it is shown that the CD spectrum of (−)-palau’amine can be explained based on the assumption that the pyrrolopyrazinone partial structure is planar in 2,2,2-trifluoroethanol (TFE). Surprisingly, the natural product (−)-dibromophakellin shows the opposite Cotton effect, despite exhibiting the same absolute configuration.
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