title: Total synthesis of flustramine C via dimethylallyl rearrangement.
abstract: 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].
authors.affiliation: Ludwig Maximilian University, Department of Chemistry and Biochemistry, Butenandtstrasse 5-13, D-81377 Munich, Germany. thomas.lindel@cup.uni-muenchen.de
authors.forename: Thomas
authors.initials: T
authors.lastname: Lindel
authors.forename: Laura
authors.initials: L
authors.lastname: Bräuchle
authors.forename: Gregor
authors.initials: G
authors.lastname: Golz
authors.forename: Petra
authors.initials: P
authors.lastname: Böhrer
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D000818:Animals; D002013:Bryozoa / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D026121:Indole Alkaloids; D007211:Indoles / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008958:Models, Molecular; D015394:Molecular Structure; D009556:Niobium / Q000737:chemistry; D010084:Oxidation-Reduction; D012680:Sensitivity and Specificity; D014363:Tryptamines / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D006575:Heterocyclic Compounds, 3-Ring; D026121:Indole Alkaloids; D007211:Indoles; D014363:Tryptamines; C473008:deformylflustrabromine; C511648:flustramine C; D009556:Niobium