Synthesis of aurachins B and H |
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Authors: | Kazuki Takahashi Shigefumi Kuwahara |
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Affiliation: | Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan |
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Abstract: | The synthesis of aurachin B, an antibiotic that features a C3-oxygen-substituted quinoline N-oxide nucleus bearing a farnesyl side chain at C4, was accomplished in 60% overall yield from o-nitrotoluene by a concise five-step sequence. An enantioselective synthesis of aurachin H was also achieved for the first time in only two steps from an optically active epoxy iodide. |
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Keywords: | aurachin B aurachin H quinoline antibiotics reductive cyclization quinoline N-oxide |
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