Total synthesis of the 7,3'-linked naphthylisoquinoline alkaloid ancistrocladidine.
The first total synthesis of ancistrocladidine, a rare 7,3'-linked naphthylisoquinoline alkaloid, has been completed, with the key feature of the synthesis being the formation of the extremely hindered biaryl linkage by ortho-arylation of a naphthol with an aryllead triacetate. Initial efforts were focused on the generation of a heteroaryl lead species, which would have allowed a convergent synthesis to be developed. However, it was not possible to generate such a lead species. A simpler aryl lead triacetate was prepared and reacted. The resulting biaryl aldehyde was 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
School of Chemistry and Physics, University of Adelaide, Adelaide, SA, Australia, and Department of Chemistry, University of Canterbury, Christchurch, New Zealand.
Morris
Jonathan C
JC
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D007546:Isoquinolines; D009284:Naphthols; C451486:ancistrocladidine