Total synthesis of flustramine C via dimethylallyl rearrangement.
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].
Lindel
Thomas
T
Ludwig Maximilian University, Department of Chemistry and Biochemistry, Butenandtstrasse 5-13, D-81377 Munich, Germany. thomas.lindel@cup.uni-muenchen.de
Bräuchle
Laura
L
Golz
Gregor
G
Böhrer
Petra
P
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*
D000498:Allyl Compounds; D006575:Heterocyclic Compounds, 3-Ring; D026121:Indole Alkaloids; D007211:Indoles; D014363:Tryptamines; C473008:deformylflustrabromine; C511648:flustramine C; D009556:Niobium