A Bioinspired Synthesis of (±)-Rubrobramide, (±)-Flavipucine, and (±)-Isoflavipucine.

  title={A Bioinspired Synthesis of (±)-Rubrobramide, (±)-Flavipucine, and (±)-Isoflavipucine.},
  author={Shoma Mizutani and Kenta Komori and Tohru Taniguchi and Kenji Monde and Kouji Kuramochi and Kazunori Tsubaki},
  journal={Angewandte Chemie},
  volume={55 33},
A biomimetic synthesis of naturally occurring lactams rubrobramide, flavipucine, and isoflavipucine is described. The key step is a regioselective Darzens reaction between isobutyl glyoxal and an α-bromo-β-ketoamide. The construction of the core tricyclic ring system of rubrobramide was achieved by a cascade reaction in a single step from an α,β-epoxy-γ-lactam. Furthermore, the absolute configuration of naturally occurring (+)-rubrobramide was determined by vibrational circular dichroism… Expand
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  • J. Findlay, L. Radics
  • Chemistry, Medicine
  • Journal of the Chemical Society. Perkin transactions 1
  • 1972
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