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Total Synthesis of Flustramine C via Dimethylallyl Rearrangement

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journal contribution
posted on 18.01.2007, 00:00 by Thomas Lindel, Laura Bräuchle, Gregor Golz, Petra Böhrer
The marine natural product flustramine C from the bryozoan Flustra foliacea was synthesized in five steps and 38% yield starting from Nb-methyltryptamine. The key step is the biomimetic oxidation of the natural product deformylflustrabromine causing selective 1,2-rearrangement of the inverse prenyl group. By 1H,15N HMBC experiments, it is unambiguously shown that the reaction with t-BuOCl commences with chlorination of the side chain nitrogen. Deformylflustrabromine itself was synthesized via Danishefsky inverse prenylation.