Syntheses of tetrahydrofurobenzofurans and dihydromethanobenzodioxepines from 5-hydroxy-3-methyl-3H-benzofuran-2-one. Rearrangement and ring expansion under reductive conditions on treatment with hydrides.

@article{Luo2005SynthesesOT,
  title={Syntheses of tetrahydrofurobenzofurans and dihydromethanobenzodioxepines from 5-hydroxy-3-methyl-3H-benzofuran-2-one. Rearrangement and ring expansion under reductive conditions on treatment with hydrides.},
  author={Weiming Luo and Qian-sheng Yu and Harold W. Holloway and Damon A. Parrish and Nigel H. Greig and Arnold Brossi},
  journal={The Journal of organic chemistry},
  year={2005},
  volume={70 16},
  pages={6171-6}
}
5-Hydroxy-3-methyl-3H-benzofuran-2-one, 5, easily obtained from pyruvic acid and 1,4-cyclohexanedione, was used as a starting material to prepare (+/-)-5-hydroxy-3a-methyl-2,3,3a,8a-tetrahydro-furo[2,3-b]benzofuran, 10, and (+/-)-7-hydroxy-5-methyl-4,5-dihydro-2,5-methano-1,3-benzodioxepine, 14. Reduced reactivity relative to 5-hydroxy-3-methoxycarbonylmethylene-3-methyl-3H-benzofuran-2-one, 6, was preliminarily studied. Meanwhile, a plausible mechanism with regard to the formation of 10 and 14… CONTINUE READING