Total synthesis of the 7,3'-linked naphthylisoquinoline alkaloid ancistrocladidine |
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Authors: | Bungard Christopher J Morris Jonathan C |
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Affiliation: | School of Chemistry and Physics, University of Adelaide, Adelaide, SA, Australia, and Department of Chemistry, University of Canterbury, Christchurch, New Zealand. |
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Abstract: | 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. |
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