Efficient total synthesis of 12-oxo-PDA and OPC-8:0.

@article{Ainai2003EfficientTS,
  title={Efficient total synthesis of 12-oxo-PDA and OPC-8:0.},
  author={Takayuki Ainai and Michitaka Matsuumi and Yuichi Kobayashi},
  journal={The Journal of organic chemistry},
  year={2003},
  volume={68 20},
  pages={7825-32}
}
Although the supply of 12-oxo-PDA (1) and OPC-8:0 (2), the metabolites in the linolenic acid cascade leading to epi-jasmonic acid, is in demand for biological investigations, the previous syntheses of these metabolites suffer from low efficiency. Recently, we established a reaction to install an alkyl group onto the ring of cyclopentene monoacetate 4 by using a reagent system consisting of RMgCl (3 equiv) and CuCN (cat). The reaction was applied to ClMg(CH2)8OTBDPS (11) with modification by… CONTINUE READING

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