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Unsymmetrical vic ‐Tricarbonyl Compounds for the Total Syntheses of Cladoniamide G and Cladoniamide F
Author(s) -
Schütte Julia,
Kilgenstein Frank,
Fischer Michel,
Koert Ulrich
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402531
Subject(s) - chemistry , amide , intramolecular force , enantiomer , natural product , enantioselective synthesis , indole test , stereochemistry , suzuki reaction , total synthesis , lactam , catalysis , stereoisomerism , organic chemistry , palladium
A 2‐unsubstituted indole adds under Cu‐box‐catalysis to mesoxalic ester amides with high enantioselectivity, whereas low enantiomeric excess is obtained for 2‐substituted indoles. A mesoxalic ester amide is used as key component in the total syntheses of alkaloids cladoniamide G and cladoniamide F. The natural product syntheses involve Suzuki cross‐coupling to a 2,2′‐biindole, arylation of the vic ‐tricarbonyl compound, and intramolecular lactam formation.