Synthesis and stereochemistry of JBIR-81, a peptide enamide derived from aspergilli |
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| Authors: | Ryo Katsuta Mami Toyoda Arata Yajima Ken Ishigami Tomoo Nukada |
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| Institution: | 1. Department of Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya-ku, Tokyo 156-8502, Japan;2. Graduate School of Agriculture, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya-ku, Tokyo 156-8502, Japan |
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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% 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. |
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| Keywords: | Enamide Synthesis Stereochemistry Aspergillus Buchwald coupling JPCCPHMRNLOTIF-RYUDHWBXSA-N IODNETMCEHQSGF-POJYLLKHSA-N IODNETMCEHQSGF-RGISFYSBSA-N |
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