Syntheses of cerulenin and its analogs. II. Synthesis and biological activity of dl-carbacerulenin, a carbocyclic analog of cerulenin.

@article{Shimazawa1992SynthesesOC,
  title={Syntheses of cerulenin and its analogs. II. Synthesis and biological activity of dl-carbacerulenin, a carbocyclic analog of cerulenin.},
  author={Rumiko Shimazawa and Yuka Ogawa and Naoko Morisaki and Hiroshi Funabashi and Akihiko Kawaguchi and Shigeo Iwasaki},
  journal={Chemical \& pharmaceutical bulletin},
  year={1992},
  volume={40 11},
  pages={
          2954-7
        }
}
2,3-Epoxy-4-hydroxy-4-((E,E)-3,6-octadienyl)cyclopentanone (dl-carbacerulenin 5) was synthesized via the epoxyketones 15a and 15b as a mimic of the active form of the antibiotics cerulenin 1, a potent inhibitor of fatty acid synthetase (FAS). The monobenzyl ethers (12 and 13), synthetic intermediates of 15, were prepared by direct benzylation of the epoxycyclopentene (7). Inhibitory activity of synthesized 5 toward yeast FAS was less than that of cerulenin by a factor of 1000. 
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