Lindel Thomas, Bräuchle Laura, Golz Gregor, Böhrer Petra
Ludwig Maximilian University, Department of Chemistry and Biochemistry, Butenandtstrasse 5-13, D-81377 Munich, Germany.
Org Lett. 2007 Jan 18;9(2):283-6. doi: 10.1021/ol0627348.
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. [reaction: see text].
