Unsymmetrical  vic ‐Tricarbonyl Compounds for the Total Syntheses of Cladoniamide G and Cladoniamide F | Zendy

Schütte Julia | Zendy; Kilgenstein Frank | Zendy; Fischer Michel | Zendy; Koert Ulrich | Zendy

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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.

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