First total synthesis of the 7,3'-linked naphthylisoquinoline alkaloid ancistrocladidine.
[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.
Bungard
Christopher J
CJ
Department of Chemistry, University of Canterbury, Christchurch, New Zealand.
Morris
Jonathan C
JC
D002384:Catalysis; D007202:Indicators and Reagents; D007546:Isoquinolines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D009284:Naphthols / Q000138:chemical synthesis*; D010946:Plants, Medicinal / Q000737:chemistry*
D007202:Indicators and Reagents; D007546:Isoquinolines; D009284:Naphthols; C451486:ancistrocladidine