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Biomimetic Total Synthesis of Lamellarin L by Coupling of Two Different Arylpyruvic Acid Units
Author(s) -
Peschko Christian,
Winklhofer Christian,
Steglich Wolfgang
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(20000403)6:7<1147::aid-chem1147>3.0.co;2-1
Subject(s) - pyrrole , derivative (finance) , yield (engineering) , stereochemistry , chemistry , total synthesis , organic chemistry , materials science , metallurgy , financial economics , economics
Reaction of the ethyl 3‐arylpyruvate 5 a with the methyl 2‐bromo‐3‐arylpyruvate 6 b 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.