Total synthesis of 7',8'-dihydroaigialospirol

Org Lett. 2012 Oct 5;14(19):5154-7. doi: 10.1021/ol302498v. Epub 2012 Sep 27.

Abstract

A highly convergent total synthesis of 7',8'-dihydroaigialospirol is described. Key steps of the synthesis include a Nozaki-Hiyama-Kishi (NHK) coupling of an iodoalkyne with an advanced phthalide-aldehyde and a remarkable one-pot acid-mediated global deprotection/spiroacetalization.

MeSH terms

  • Aldehydes / chemistry
  • Alkenes / chemistry
  • Alkynes / chemical synthesis
  • Benzofurans / chemical synthesis*
  • Benzofurans / chemistry
  • Molecular Structure
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry

Substances

  • 7',8'-dihydroaigialospirol
  • Aldehydes
  • Alkenes
  • Alkynes
  • Benzofurans
  • Spiro Compounds
  • phthalide