Alkaloids from marine organisms, Part 5. Biomimetic total synthesis of lamellarin L by coupling of two different arylpyruvic acid units.
Reaction of the ethyl 3-arylpyruvate 5a with the methyl 2-bromo-3-arylpyruvate 6b in the presence of the 2-arylethylamine 4 afforded the pyrrole derivative 10, which could be transformed into lamellarin L (1) in five steps. The synthesis proceeds with 38% overall yield and mimics the probable biosynthesis of these marine alkaloids.
Peschko
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C. Winklhofer Institut für Organische Chemie, Universität München, Germany.
Winklhofer
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Steglich
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D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry*; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry*; D003374:Coumarins; D006576:Heterocyclic Compounds, 4 or More Rings; D007546:Isoquinolines / Q000138:chemical synthesis / Q000737:chemistry*; D008974:Mollusca / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry; D011773:Pyruvates / Q000737:chemistry*
D000470:Alkaloids; D000970:Antineoplastic Agents; D001578:Benzopyrans; D003374:Coumarins; D006576:Heterocyclic Compounds, 4 or More Rings; D007546:Isoquinolines; D011758:Pyrroles; D011773:Pyruvates; C408387:lamellarin L