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Study on the absolute configuration of (−)-palau’amine

✍ Scribed by Thomas Lindel; Delphine E.N. Jacquot; Michael Zöllinger; Robin B. Kinnel; Shayna McHugh; Matthias Köck

Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
395 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

The absolute stereochemistry of the immunosuppressive pyrrole-imidazole alkaloid (À)-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 (À)-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 (À)-dibromophakellin shows the opposite Cotton effect, despite exhibiting the same absolute configuration.

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