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Synthesis of aurachins B and H
Authors:Kazuki Takahashi  Shigefumi Kuwahara
Affiliation:Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan
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.
Keywords:aurachin B  aurachin H  quinoline antibiotics  reductive cyclization  quinoline N-oxide
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