Decarbonylative Approach to the Synthesis of Enamides from Amino Acids: Stereoselective Synthesis of the (Z)-Aminovinyl-d-Cysteine Unit of Mersacidin

Decarbonylative Approach to the Synthesis of Enamides from Amino Acids: Stereoselective Synthesis of the (Z)-Aminovinyl-d-Cysteine Unit of Mersacidin

The Pd- and Ni-promoted decarbonylation of amino acid thioesters proceeds smoothly to yield enamides. The synthesis of the (S)-(Z)-AviMeCys subunit of mersacidin, an MRSA-active lantibiotic, via this approach, is described.

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Veröffentlicht in:Organic letters 2012-02, Vol.14 (4), p.1030-1033
Hauptverfasser: García-Reynaga, Pablo, Carrillo, Angela K, VanNieuwenhze, Michael S
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemistry
Amino Acid Sequence
Amino Acids - chemistry
Bacteriocins - chemistry
Cysteine - chemistry
Molecular Sequence Data
Nickel - chemistry
Palladium - chemistry
Peptides - chemistry
Protein Carbonylation
Stereoisomerism
Vinyl Compounds - chemical synthesis
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Zusammenfassung:The Pd- and Ni-promoted decarbonylation of amino acid thioesters proceeds smoothly to yield enamides. The synthesis of the (S)-(Z)-AviMeCys subunit of mersacidin, an MRSA-active lantibiotic, via this approach, is described.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol203399x