First total synthesis of the 7,3'-linked naphthylisoquinoline alkaloid ancistrocladidine

Org Lett. 2002 Feb 21;4(4):631-3. doi: 10.1021/ol017258u.

Abstract

[structure: see text] The first total synthesis of the rare 7,3'-linked naphthylisoquinoline alkaloid, ancistrocladidine, has been completed. The key feature of the synthesis is the formation of the extremely hindered biaryl linkage by Pinhey-Barton ortho-arylation of a naphthol with an aryllead triacetate. The biaryl aldehyde formed is elaborated in 10 steps to form a 1:1 mixture of ancistrocladidine and its atropisomer. Recrystallization of the mixture afforded ancistrocladidine, which was identical in all respects to the reported data.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Indicators and Reagents
  • Isoquinolines / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Naphthols / chemical synthesis*
  • Plants, Medicinal / chemistry*

Substances

  • Indicators and Reagents
  • Isoquinolines
  • Naphthols
  • ancistrocladidine