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Synthesis and stereochemistry of JBIR-81, a peptide enamide derived from aspergilli

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Abstract The absolute stereochemistry of an aspergilli-derived peptide enamide, JBIR-81, was determined to be 12S, 15S by the first synthesis of (12S,15S)-JBIR-81 and its epimer. The overall yield was 56%… Click to show full abstract

Abstract The absolute stereochemistry of an aspergilli-derived peptide enamide, JBIR-81, was determined to be 12S, 15S by the first synthesis of (12S,15S)-JBIR-81 and its epimer. The overall yield was 56% over six steps from N-methyl- l -leucine. The (Z)-enamide structure was effectively constructed with use of a copper (I) catalyzed coupling reaction between a vinyl halide and a carboxamide.

Keywords: jbir peptide; synthesis stereochemistry; peptide enamide; stereochemistry jbir; jbir

Journal Title: Tetrahedron Letters
Year Published: 2018

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