A concise synthesis of (+/-)-cacalol.

@article{Kedrowski2008ACS,
  title={A concise synthesis of (+/-)-cacalol.},
  author={Brant L Kedrowski and Robert W Hoppe},
  journal={The Journal of organic chemistry},
  year={2008},
  volume={73 13},
  pages={5177-9}
}
A simple synthesis of the natural product cacalol has been developed that proceeds in seven steps and 21-25% overall yield. Ortho-lithiation of 4-methylanisole and alkylation with 5-iodo-1-pentene, followed by intramolecular Friedel-Crafts alkylation, gave 5-methoxy-1,8-dimethyltetralin. This compound was then formylated in the 6-position. Baeyer-Villiger oxidation and hydrolysis of the resulting formate gave 6-hydroxy-5-methoxy-1,8-dimethyltetralin. Alkylation of the phenolic hydroxyl group… CONTINUE READING

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