Toward the elucidation of the metabolism of 15-E(2)-isoprostane: the total synthesis of the methyl ester of a potential central metabolite.

@article{Jahn2010TowardTE,
  title={Toward the elucidation of the metabolism of 15-E(2)-isoprostane: the total synthesis of the methyl ester of a potential central metabolite.},
  author={Ullrich Jahn and Emanuela Dinca},
  journal={The Journal of organic chemistry},
  year={2010},
  volume={75 13},
  pages={4480-91}
}
An 11-step total synthesis of the methyl ester of a potential metabolite of the autoxidatively formed natural product 15-E(2)-IsoP, whose metabolism is not known, is reported. Several vinylogous Mukaiyama aldol additions were tested for the assembly of the acyclic C7-C20 precursor. A new oxidative dianion cyclization served to access the cyclopentane core. The full carbon skeleton was synthesized by an acetylide alkylation. The overall yield of the metabolite amounts to 1.4% for the most… CONTINUE READING